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Triethylamine → HCID 58367175, compound

HRID 1891489
Notes
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Reaction equation

HRID 1891489 reaction equation
[CH:1]1[N:5]=[CH:4][N:3]([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])[CH:2]=1.Cl.N[C@H]1C2[C:18](=[C:19]([C:24]3[S:28][C:27]([C:29]4[CH:30]=[CH:31][C:32]([O:37][CH:38]([CH3:40])[CH3:39])=[C:33]([CH:36]=4)[C:34]#[N:35])=[N:26][N:25]=3)[CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1.[CH3:41][CH2:42]N(CC)CC.Cl.N1CC(O)[CH2:50]1>C(Cl)Cl>[C:34]([C:33]1[CH:36]=[C:29]([C:27]2[S:28][C:24]([C:19]3[CH:20]=[CH:21][CH:22]=[C:10]4[C:18]=3[CH2:17][CH2:16][C@H:9]4[NH:8][C:6]([N:3]3[CH2:42][CH2:41][C@@H:1]([N:5]([CH3:4])[CH3:50])[CH2:2]3)=[O:7])=[N:25][N:26]=2)[CH:30]=[CH:31][C:32]=1[O:37][CH:38]([CH3:39])[CH3:40])#[N:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27592903-Hydroxyazetidine hydrochlorideHCID 67195507HCID 67195507, compound

Product 1

HCID 58367175HCID 58367175, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

Prepared using General Procedure 19: To a CDI ((13.4 mg, 0.08 mmol) in DCM (0.5 mL) was added a suspension of (R)-5-(5-(1-amino-2,3-dihydro-1H-inden-4-yl)-1,3,4-thiadiazol-2-yl)-2-isopropoxybenzonitrile hydrochloride 5 (20.0 mg, 0.04 mmol) and Et3N (14.7 mg, 0.14 mmol) in DCM (0.5 mL) and the mixture stirred for 2 h at room temperature. The resulting solution was added to the preparative solution of azetidin-3-ol hydrochloride (15.9 mg, 0.14 mmol)) at room temperature. The reaction was stirred at room temperature for 16 h. The solvent was evaporated and the crude material was purified by preparative HPLC to afford 15 mg of (62%) of (R)-N-((R)-4-(5-(3-cyano-4-isopropoxyphenyl)-1,3,4-thiadiazol-2-yl)-2,3-dihydro-1H-inden-1-yl)-3-(dimethylamino)pyrrolidine-1-carboxamide 56. LCMS-ESI (m/z) calculated for C28H32N6O2S: 516.2; found 517.2 [M+H]+, tR=2.43 min. 1H NMR (400 MHz, DMSO) δ 8.40 (d, J=2.4 Hz, 1H), 8.32 (dd, J=9.0, 2.4 Hz, 1H), 7.99-7.76 (m, 1H), 7.51 (d, J=9.2 Hz, 1H), 7.49-7.34 (m, 2H), 6.73 (d, J=8.4 Hz, 1H), 5.32 (d, J=8.2 Hz, 1H), 5.09-4.80 (m, 1H), 3.86 (dd, J=14.3, 7.0 Hz, 1H), 3.75 (dd, J=11.0, 7.5 Hz, 1H), 3.63-3.48 (m, 1H), 3.45-3.22 (m, 3H), 3.10 (dt, J=16.5, 8.3 Hz, 1H), 2.82 (t, J=5.1 Hz, 6H), 2.56-2.40 (m, 1H), 2.32 (dd, J=9.8, 2.5 Hz, 1H), 2.15-2.02 (m, 1H), 2.00-1.81 (m, 1H), 1.38 (d, J=6.0 Hz, 6H). 13C NMR (101 MHz, CDCl3) δ 167.10, 165.84, 161.80, 145.94, 142.30, 133.54, 133.36, 128.86, 127.82, 126.94, 126.41, 122.72, 115.78, 114.01, 103.72, 72.71, 64.71, 55.95, 46.76, 44.20, 42.04, 34.06, 31.45, 27.30, 21.90, 21.89.

Workup

  1. customPrepared
  2. stirringThe reaction was stirred at room temperature for 16 h
  3. customThe solvent was evaporated
  4. customthe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-1ad33eaff26a40c28c83ac2bc5611bef
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507538B2

Reaction notes

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