1,1'-Carbonyldiimidazole → HCID 66970659, compound

HRID 1363224Notes

Reaction equation

HRID 1363224 reaction equation
[NH2:1][C:2]1[C:3]([NH:18][C@H:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22](=[O:29])[CH2:21][CH2:20]2)=[N:4][C:5]([N:8]2[C:12]3[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)=[N:6][CH:7]=1.C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1>C1COCC1>[F:17][C:14]1[CH:15]=[CH:16][C:11]2[N:10]=[CH:9][N:8]([C:5]3[N:4]=[C:3]4[C:2]([NH:1][C:35](=[O:36])[N:18]4[C@H:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:22](=[O:29])[CH2:21][CH2:20]4)=[CH:7][N:6]=3)[C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66970418HCID 66970418, compound

Product 1

HCID 66970659HCID 66970659, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (4R)-4-(5-amino-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidin-4-ylamino)-3,4-dihydronaphthalen-1(2H)-one (32 mg) and CDI (100 mg) in THF (6 mL) was stirred at room temperature overnight and refluxed for 2.5 h. Volatiles were removed in vacuo and the residue was purified by preparative HPLC to afford 9 mg of the title compound as the TFA salt. 1H NMR (CD3OD) δ 9.20 (s, 1H), 8.36 (s, 1H), 8.20 (m, 1H), 7.68 (m, 1H), 7.58-7.47 (m, 3H), 7.20-7.14 (m, 2H), 6.10 (m, 1H), 3.09-2.93 (m, 3H), 2.49 (m, 1H); MS (MH+) 415.1.

Workup

  1. temperaturerefluxed for 2.5 h
  2. customVolatiles were removed in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a29c8a61728c4643ae675c5474666d42
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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