Dimethylformamide dimethyl acetal → HCID 67312969, compound

HRID 222038Notes

Reaction equation

HRID 222038 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][CH2:28][C:29](=[O:31])[CH2:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1.CO[CH:34](OC)[N:35]([CH3:37])[CH3:36]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][CH2:28][C:29](=[O:31])/[C:30](=[CH:34]\[N:35]([CH3:37])[CH3:36])/[C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 58346666HCID 58346666, compound

Product 1

HCID 67312969HCID 67312969, compound

Procedure

The title compound was prepared following the method described for example 98 step 4, utilizing 4-({3-chloro-4-[(6-methylpyridin-2-yl)methoxy]phenyl}amino)-5,8-dihydro[1]benzothieno[2,3-d]pyrimidin-7(6H)-one (435 mg, 1.0 mmol) and dimethylformamide-dimethylacetal (230 mg, 1.9 mmol). The desired product was collected as a yellow solid (302 mg, 62%). 1H-NMR (DMSO-d6) (major rotomer) δ 8.26 (s, 1H), 8.18 (s, 1H), 7.75 (d, 1H), 7.72 (d, 1H), 7.51 (dd, 1H), 7.34 (d, 1H), 7.21 (d, 1H), 7.18 (d, 1H), 7.07 (s, 1H), 5.21 (s, 2H), 3.27 (t, 2H), 3.12 (s, 3H), 3.09 (s, 3H), 2.57 (t. 2H); LCMS RT=2.38 min; [M+H]+=506.1.

Workup

  1. customThe desired product was collected as a yellow solid (302 mg, 62%)

Sources & evidence

ORD record
ord-8287ebfdb5b545b396212715ce0cbdfe
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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