Diisopropylethylamine → HCID 178463584, compound

HRID 408805Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

1-[3-(3,5-Difluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]ethanamine trifluoroacetate (16 mg, 0.07 mmol), 6-bromo-9H-purine (13 mg, 0.07 mmol, Aldrich 104981) and N,N-diisopropylethylamine (12 mL, 0.07 mmol) were stirred in ethanol (0.47 mL) and heated to 110° C. for 16 hours. Purification by preparative LCMS (H2O with 0.1% TFA (pH 2), 5% acetonitrile to 24% acetonitrile over 1 minute, 24% to 48% acetonitrile over 12 minutes, Waters Sunfire C18, 5 μM particle size, 30×100 mm, RT=8.75 min.) gave the desired compound (4.0 mg, 12%). LCMS for C20H17F2N7 (M+H)+: m/z=392.0. 1H NMR (300 MHz, DMSO-d6): 8.75 (m, 1H), 8.39 (m, 1H), 8.28 (m, 1H), 7.64 (m, 1H), 7.31 (m, 1H), 7.23 (m, 2H), 7.17 (m, 1H), 6.98 (m, 1H), 5.84 (m, 1H), 1.62 (m, 3H).

Workup

customPurification by preparative LCMS (H2O with 0.1% TFA (pH 2), 5% acetonitrile to 24% acetonitrile over 1 minute, 24% to 48% acetonitrile over 12 minutes, Waters Sunfire C18, 5 μM particle size, 30×100 mm, RT=8.75 min.)

Sources & evidence

ORD record: ord-cdb94440e225433c8130f068cab6da63
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759359B2

Reaction notes

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