Triethylamine → HCID 178522792, compound

HRID 1672493Notes

Reaction equation

HRID 1672493 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.[CH:29]1([S:32](Cl)(=[O:34])=[O:33])[CH2:31][CH2:30]1.C(N(CC)CC)C.ClC(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][S:32]([CH:29]4[CH2:31][CH2:30]4)(=[O:34])=[O:33])[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 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 86639583HCID 86639583, compoundHCID 178511657HCID 178511657, compound

Product 1

HCID 178522792HCID 178522792, compoundYield 10.2%

Procedure

A solution of 2-[(trans-4-aminocyclohexyl)amino]-N-benzylquinazoline-7-carboxamide (200.0 mg, 0.53 mmol), cyclopropanesulfonyl chloride (37.4 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 prepHPLC to give 13.0 mg of the product (yield 10.2%). 1H NMR (400 MHz, DMSO-d6) ppm 0.78-1.06 (m, 6H), 1.39 (t, J=9.82 Hz, 4H), 1.99 (d, J=4.28 Hz, 3H), 2.37-2.48 (m, 1H), 2.54-2.64 (m, 1H), 3.13 (s, 1H), 3.78 (s, 1H), 4.18 (d, J=6.55 Hz, 1H), 4.50 (d, J=6.04 Hz, 1H), 7.08 (d, J=7.81 Hz, 1H), 7.22-7.30 (m, 1H), 7.31-7.37 (m, 6H), 7.43-7.50 (m, 1H), 7.64 (d, J=6.80 Hz, 1H), 7.85 (d, J=8.31 Hz, 1H), 8.00 (s, 1H), 9.14 (s, 1H), 9.29 (t, J=5.92 Hz, 1H). HRMS: m/z 480.20484 [M+H]+), calc. 480.20638. MS m/z, (APCI); 480.2 ([M+H]+).

Workup

  1. customThe crude material was purified by prepHPLC

Sources & evidence

ORD record
ord-0f9c40c6a1784c19810e9594ca229ee3
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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