Triethylamine → HCID 44256300, compound

HRID 2189460Notes

Reaction equation

HRID 2189460 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[N:20]5[CH:21]=[CH:22]C=[C:24]([C:25](O)=[O:26])[C:19]5=[N:18][N:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.C1C=CC2N(O)N=[N:36]C=2C=1.Cl.[NH2:41][C@@H:42]([CH2:45][CH3:46])[CH2:43][OH:44].C(N(CC)CC)C>CN(C=O)C.C(Cl)CCl.C(Cl)Cl>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[N:20]5[CH:21]=[CH:22][N:36]=[C:24]([C:25]([NH:41][C@@H:42]([CH2:45][CH3:46])[CH2:43][OH:44])=[O:26])[C:19]5=[N:18][N:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole2×HCID 120083(S)-(+)-2-Amino-1-butanol hydrochlorideHCID 58137788HCID 58137788, compound

Product 1

HCID 44256300HCID 44256300, compoundYield 6.1%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-(4-(6-chlorobenzo[d]thiazol-2-ylamino)phenyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid (63E) (43 mg, 0.1 mmol), EDC (24.4 mg, 0.127 mmol) and HOBt (17.2 mg, 0.127 mmol) in DMF (1 mL) was stirred for 5 min, and then (S)-2-aminobutan-1-ol, hydrochloride salt (13 mg, 0.104 mmol) and triethylamine (20.6 mg, 0.203 mmol) were added. The mixture was stirred at room temperature overnight. To the reaction mixture was added anhydrous DCM (1 mL), followed by additional EDC (25 mg) and HOBt (17 mg). The resulting mixture was then stirred for additional 2 h before concentrated in vacuo. The crude product was purified by preparative HPLC using MeOH/H2O/TFA solvent system to yield the title compound (3 mg). HPLC/MS (Method C): retention time=2.14 min (broad rotomer), [M+H]+=494.1. 1H NMR (500 MHz, DMSO-d6): δ 10.97 (s, 1H), 8.98 (d, J=8.25 Hz, 1H), 8.77 (d, J=4.95 Hz, 1H), 8.02-8.09 (m, 3H), 7.93-8.01 (m, 3H), 7.64 (d, J=8.80 Hz, 1H), 7.38 (dd, J=8.80, 2.20 Hz, 1H), 3.94-4.03 (m, 1H), 3.57 (dd, J=10.72, 4.67 Hz, 1H), 3.48 (dd, J=11.00, 5.50 Hz, 1H), 1.48-1.61 (m, 1H). 0.89-1.02 (m, 3H).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. stirringThe resulting mixture was then stirred for additional 2 h
  3. concentrationbefore concentrated in vacuo
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-963066769b014e2c8e27bb14c51cfca7
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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