Methanol → HCID 68779395, compound

HRID 1042292

Reaction equation

[F:1][C:2]1([F:12])[O:6][C:5]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:4]=2[O:3]1.[NH:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([C:22]3[C:23]([NH:28][C:29]4[C:30]5[CH:31]=[CH:32][N:33]=[C:34](Cl)[C:35]=5[CH:36]=[CH:37][C:38]=4[CH3:39])=[N:24][CH:25]=[CH:26][CH:27]=3)=[C:16]2[CH:15]=[N:14]1.FC(F)(F)C(O)=O.CO>CC(O)C.CCN(CC)CC>[NH:13]1[C:17]2=[N:18][CH:19]=[N:20][C:21]([C:22]3[C:23]([NH:28][C:29]4[C:30]5[CH:31]=[CH:32][N:33]=[C:34]([NH:11][C:9]6[CH:8]=[CH:7][C:5]7[O:6][C:2]([F:1])([F:12])[O:3][C:4]=7[CH:10]=6)[C:35]=5[CH:36]=[CH:37][C:38]=4[CH3:39])=[N:24][CH:25]=[CH:26][CH:27]=3)=[C:16]2[CH:15]=[N:14]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2,2-difluorobenzo[d][1,3]dioxol-5-amine (64 mg, 371 mop, N-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-1-chloro-6-methylisoquinolin-5-amine (120 mg, 309 μmol) and 2,2,2-trifluoroacetic acid (95 μl, 1238 μmol) in i-PrOH (4 ml) was heated in a microwave reactor at 150° C. for 40 min. The mixture was poured into MeOH (10 ml) and Et3N (0.25 ml) was added. Solvent was removed under vacuum and the product was purified by flash chromatography eluting with MeOH/DCM (1-5%) to give N5-(3-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)pyridin-2-yl)-N1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-6-methylisoquinoline-1,5-diamine. MS Found: (ESI pos. ion) m/z 525 (M+H+).

Workup

additionwas added
customSolvent was removed under vacuum
customthe product was purified by flash chromatography
washeluting with MeOH/DCM (1-5%)

Sources & evidence

ORD record: ord-f9900f46dbbd4efc822e74401859a9bf
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557830B2

Linked notes

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