Isopropyl isocyanate → HCID 67091752, compound

HRID 2074094Notes

Reaction equation

[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([NH2:21])[CH2:17][CH2:16]3)=[O:14])[N:10]=[C:9]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:8]=2)=[CH:4][CH:3]=1.[CH:30]([N:33]=[C:34]=[O:35])([CH3:32])[CH3:31]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:16][CH2:17][CH:18]([NH:21][C:34]([NH:33][CH:30]([CH3:32])[CH3:31])=[O:35])[CH2:19][CH2:20]3)=[O:14])[N:10]=[C:9]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[CH:8]=2)=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine (635 mg, 1.61 mmol) in THF (10 mL) at room temperature was added isopropyl isocyanate (164 mg, 1.93 mmol) and the solution stirred 50° C. for 16 h. The volatiles were removed under vacuum and the residue was triturated with water to afford a white solid, 627 mg, 82%.1H NMR (400 MHz, DMSO-d6) δ ppm 1.02 (d, J=6.55 Hz, 6 H), 1.08-1.21 (m, J=7.18, 7.18 Hz, 1 H), 1.23-1.39 (m, 1 H), 1.65-1.90 (m, 2 H), 2.81 (t, J=10.95 Hz, 1 H), 3.05-3.25 (m, J=11.33, 11.33 Hz, 1 H), 3.50-3.72 (m, 2 H), 3.80 (d, J=13.60 Hz, 1 H), 3.95 (s, 2 H), 4.07 (d, J=13.35 Hz, 1 H), 5.03-5.33 (m, 2 H), 5.58 (d, J=7.81 Hz, 1 H), 5.75 (d, J=7.81 Hz, 1 H), 6.56 (s, 1 H), 7.02-7.26 (m, 2 H), 7.22-7.40 (m, 2 H), 7.64-7.79 (m, 2 H), 8.56 (d, J=6.04 Hz, 2 H); m/z (APCI+) for C26H31FN6O2 479.6 (M+H)+.

Workup

customThe volatiles were removed under vacuum
customthe residue was triturated with water
customto afford a white solid, 627 mg, 82%

Sources & evidence

ORD record: ord-4560133bea644524b03b0d7ac12e884e
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919488B2

Reaction notes

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