Isopropyl isocyanate → HCID 57812532, compound

HRID 911974Notes

Reaction equation

HRID 911974 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:13]1[C:14]2[O:22][CH:21]=[C:20]([C:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=3)[C:15]=2[CH:16]=[N:17][C:18]=1[NH2:19])[CH3:11].[CH:29]([N:32]=[C:33]=[O:34])([CH3:31])[CH3:30].CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:19][C:18]1[N:17]=[CH:16][C:15]2[C:20]([C:23]3[CH2:24][CH2:25][N:26]([C:33]([NH:32][CH:29]([CH3:31])[CH3:30])=[O:34])[CH2:27][CH:28]=3)=[CH:21][O:22][C:14]=2[C:13]=1[O:12][C@@H:10]([C:3]1[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[Cl:1])[CH3:11]

Participants

5

Reactant 3

HCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 57812480HCID 57812480, compound

Product 1

HCID 57812532HCID 57812532, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)-furo[3,2-c]pyridin-6-ylamine (10.0 mg, 0.0237 mmol), isopropyl isocyanate (0.00371 g, 0.0436 mmol), DIPEA (33 μL, 0.19 mmol) and DMF (1 mL) and the reaction mixture was stirred at rt for 15 min. Purification by HPLC followed by prep TLC in 5% NH3 in DCM afforded the title compound. 1H NMR (400 MHz, CD3OD): δ=1.17 (d, J=6.6 Hz, 6H), 1.88 (d, J=6.8 Hz, 3H), 2.49 (br. s., 2H), 3.63 (t, J=5.7 Hz, 2H), 3.87-3.99 (m, 1H), 4.06 (d, J=2.5 Hz, 2H), 6.13 (d, J=7.6 Hz, 1H), 6.25 (br. s., 1H), 6.49 (d, J=6.8 Hz, 1H), 7.21 (t, J=8.6 Hz, 1H), 7.39 (dd, J=9.0, 4.9 Hz, 1H), 7.63 (s, 1H). MS (ES+): m/z 507.04/509.06 (100/71) [MH+]. HPLC: tR=3.14 min (ZQ3, polar—5 min).

Workup

  1. customPurification by HPLC

Sources & evidence

ORD record
ord-d99d388d723c4d83b3a55cff071a523b
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

Loading…