Acetyl chloride → HCID 178474994, compound

HRID 1672496Notes

Reaction equation

HRID 1672496 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[CH:12][C:13]([C:19]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])=[CH:14][CH:15]=3)[N:10]=2)[CH2:4][CH2:3]1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C.ClC(Cl)C.C(COC)OC>>[C:29]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[CH:12][C:13]([C:19]([NH:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[O:20])=[CH:14][CH:15]=3)[N:10]=2)[CH2:6][CH2:7]1)(=[O:31])[CH3:30]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86639583HCID 86639583, compoundHCID 178511657HCID 178511657, compound

Product 1

HCID 178474994HCID 178474994, compoundYield 13.6%

Procedure

A solution of 2-[(trans-4-aminocyclohexyl)amino]-N-benzylquinazoline-7-carboxamide (prepared as described in preparation 7c above) (200.0 mg, 0.53 mmol), acetyl chloride (27.3 mg, 0.53 mmol) and triethylamine (162.0 mg, 1.6 mmol) in 7 ml of a mixed solvents of dichloroethane:dimethoxyethane (1:2) was stirred at room temperature for 16 hours. The crude material was purified by HPLC to give product 15.1 mg, 13.6%. 1H NMR (400 MHz, DMSO-d6) ppm 1.13-1.49 (m, 4H), 1.79 (s, 3H), 1.82 (s, 3H), 1.98 (s, 1H), 3.22-3.41 (m, 4H), 3.43-3.59 (m, 1H), 3.90 (s, 1H), 4.50 (d, J=6.04 Hz, 1H), 7.17-7.29 (m, 1H), 7.31-7.37 (m, 4H), 7.44 (d, J=8.31 Hz, 1H), 7.63 (dd, J=8.18, 1.38 Hz, 1H), 7.75 (d, J=7.81 Hz, 1H), 7.84 (d, J=8.31 Hz, 1H), 7.99 (s, 1H), 9.14 (s, 1H), 9.30 (t, J=5.79 Hz, 1H). HRMS: m/z 418.22213 [M+H]+), calc. 418.22375. MS m/z, (APCI); 418.2 ([M+H]+).

Workup

  1. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-1b19044481754216b8cbb85ec9b4129c
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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