Trifluoroacetic acid → HCID 44223173, compound

HRID 2196651Notes

Reaction equation

C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22](O)[C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([NH:32][C:33](=[O:49])[C:34]4[C:39]([F:40])=[CH:38][CH:37]=[C:36]([NH:41][S:42]([CH2:45][CH2:46][CH3:47])(=[O:44])=[O:43])[C:35]=4[F:48])[CH:30]=3)[NH:25][CH:24]=2)=[CH:18][CH:17]=1>CC#N>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][C:23]2[C:31]3[C:26](=[N:27][CH:28]=[C:29]([NH:32][C:33](=[O:49])[C:34]4[C:39]([F:40])=[CH:38][CH:37]=[C:36]([NH:41][S:42]([CH2:45][CH2:46][CH3:47])(=[O:44])=[O:43])[C:35]=4[F:48])[CH:30]=3)[NH:25][CH:24]=2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Triethylsilane (0.0590 mL, 0.355 mmol) and trifluoroacetic acid (“TFA”; 0.0180 mL, 0.234 mmol) were added to N-(3-((4-chlorophenyl)(hydroxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.005 g, 0.009 mmol) in CH3CN (1 mL). The solution was warmed to 80° C. for 10 minutes. The solution was cooled and concentrated under reduced pressure to provide N-(3-(4-chlorobenzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (4 mg, 82.5%). 1H NMR (400 MHz, CD3OD) δ 8.63-8.44 (m, 1H), 8.30-8.32 (m, 1H), 7.62-7.68 (m, 1H), 7.35 (s, 1H), 7.27 (s, 4H), 7.10-7.15 (m, 1H), 4.11 (s, 2H), 3.09-3.13 (m, 2H), 1.84-1.89 (m, 2H), 1.03-1.07 (m, 3H); m/z (APCI-pos) M+1=519.1.

Workup

temperatureThe solution was cooled
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c587f73bae284567ad797ff772e82275
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338452B2

Reaction notes

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