Diisopropylethylamine → HCID 67518314, compound

HRID 919650Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([N:7]2[C:11]3=[N:12][CH:13]=[N:14][C:15]([NH2:16])=[C:10]3[CH:9]=[N:8]2)[CH2:2]1.[Cl:17][C:18]1[CH:19]=[C:20]([NH:25][CH2:26][C:27](O)=[O:28])[CH:21]=[C:22]([Cl:24])[CH:23]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[NH2:16][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:7]([CH:3]3[CH2:4][CH2:5][CH2:6][N:1]([C:27](=[O:28])[CH2:26][NH:25][C:20]4[CH:19]=[C:18]([Cl:17])[CH:23]=[C:22]([Cl:24])[CH:21]=4)[CH2:2]3)[N:8]=[CH:9][C:10]=12

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (620 mg, 2.2 mmol), 2-((3,5-dichlorophenyl)amino)acetic acid (475 mg, 2.2 mmol, 1 eq), HBTU (822 mg, 2.2 mmol, 1 eq) and DIPEA (560 mg, 4.4 mmol, 2.0 eq) in THF (10 mL) was heated to 50° C. for 16 h. The mixture was concentrated in vacuo and purified by silica gel column with EA in PE (20% to 100%, v/v) to give the title product (63 mg, yield: 7%). 1H NMR (400 MHz, DMSO-d6) δ: 8.21 (d, 1H), 8.11 (d, 1H), 7.85-7.65 (m, 2H), 6.76 (s, 1H), 6.73 (s, 1H), 6.60 (d, 1H), 6.32 (t, 1H), 4.76-4.71 (m 0.5H), 4.61-4.54 (m, 1H), 4.48 (d, 0.5H), 4.19 (d, 0.5H), 4.11-4.08 (m, 1H), 4.02-3.94 (m, 1.5H), 3.86-3.81 (m, 0.5H), 3.17-3.09 (m, 1H), 2.95-2.90 (m, 0.5H), 2.20-2.12 (m, 1H), 2.08-2.05 (m, 1H), 1.89-1.82 (m, 1H), 1.72-1.51 (m, 1H). ESI-MS: 420.1 (M+H)+.

Workup

concentrationThe mixture was concentrated in vacuo
custompurified by silica gel column with EA in PE (20% to 100%, v/v)

Sources & evidence

ORD record: ord-230f5c8aae604cffb66a7811a4a59f9b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273028B2

Reaction notes

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