Acetyl chloride → HCID 178454571, compound

HRID 1672497Notes

Reaction equation

HRID 1672497 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])C.C(N([CH2:38][CH3:39])CC)C.Cl[CH:41](Cl)C.C(COC)OC>>[CH2:22]([NH:21][C:19]([C:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[N:18][C:9]([NH:8][C@H:5]3[CH2:4][CH2:3][C@H:2]([NH:1][C:29](=[O:31])[CH:38]([CH3:39])[CH3:41])[CH2:7][CH2:6]3)=[N:10]2)=[CH:15][CH:14]=1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 4

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

Product 1

HCID 178454571HCID 178454571, compoundYield 9.5%

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 (56.8 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 21.0 mg, 9.5%. 1H NMR (400 MHz, DMSO-d6) ppm 0.86-0.90 (m, 1H), 0.94 (s, 3H), 0.96 (s, 3H), 0.97-1.00 (m, 1H), 1.16-1.42 (m, 4H), 1.64-1.99 (m, 8H), 2.15-2.39 (m, 2H), 2.45-2.56 (m, 1H), 4.36-4.62 (m, 4H), 7.19-7.30 (m, 1H), 7.30-7.41 (m, 6H), 7.60 (d, J=7.81 Hz, 1H), 8.26 (dd, J=8.56, 1.51 Hz, 1H), 8.37 (d, J=8.56 Hz, 1H), 8.45-8.67 (m, 1H), 9.54 (t, J=5.79 Hz, 1H), 9.66-10.04 (m, 1H). HRMS: m/z 446.25321 [M+H]+), calc. 446.25505. MS m/z, (APCI); 446.2 ([M+H]+).

Workup

  1. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-e55c156e2b7b40558d1e4199d074668d
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

Loading…