Methanesulfonyl chloride → HCID 17990097, compound

HRID 1292963Notes

Reaction equation

HRID 1292963 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([NH:21][C:22]2[C:23]3[C:30]4[CH2:31][CH2:32][CH:33]([CH2:35][CH2:36][OH:37])[CH2:34][C:29]=4[S:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>C(Cl)Cl>[Cl:6][C:7]1[CH:8]=[C:9]([NH:21][C:22]2[C:23]3[C:30]4[CH2:31][CH2:32][CH:33]([CH2:35][CH2:36][O:37][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:34][C:29]=4[S:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 17990057HCID 17990057, compound

Product 1

HCID 17990097HCID 17990097, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.48 mL, 707 mg, 6.17 mmol, 1.2 equiv.) was added to a suspension of 2-{4-[3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl}-ethanol (2.4 g, 5.14 mmol, 1 equiv.) in anhydrous DCM (20 mL) at 0° C. The resulting mixture was stirred overnight during which time it was warmed to ambient temperature. The standard aqueous work-up gave Methanesulfonic acid 2-{4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl}-ethyl ester as a slight yellow solid (2.3 g, 79%). 1H-NMR (CD3OD) δ 8.56 (s, 1H), 8.33 (s, 1H), 7.85 (t, 1H), 7.79 (d, J=2.4 Hz, 1H), 7.55 (d, J=7.9 Hz, 1H), 7.51 (dd, J=2.5, 9.1 Hz, 1H), 7.34 (m, 1H), 7.20 (d, J=8.8 Hz, 1H), 5.27 (s, 2H), 4.35 (t, 2H), 3.19 (s, 3H), 3.15 (m, 3H), 2.97 (m, 1H), 2.17 (m, 2H), 1.81 (m, 2H), 1.54 (m, 1H).; LCMS RT=3.03 min; [M+H]+=545.

Sources & evidence

ORD record
ord-bac170f917fa42b5ac86d2362d754078
Source dataset
uspto-grants-2007_07
Patent number
US07238701B2

Reaction notes

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