Isopropyl isocyanate → HCID 67030769, compound

HRID 1959978Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:25])=[C:8](C(OC(C)(C)C)=O)[N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[CH:26]([N:29]=[C:30]=[O:31])([CH3:28])[CH3:27]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:25][C:30]([NH:29][CH:26]([CH3:28])[CH3:27])=[O:31])=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 61277Isopropyl isocyanate

HCID 58271024HCID 58271024, compound

Product 1

HCID 67030769HCID 67030769, compoundYield 55%

Procedure

Following general method 4, employing 3-amino-1-(3-fluorophenyl)-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester and isopropyl isocyanate, afforded the title compound as an off-white solid (0.150 g, 55%); LCMS (method B): RT=3.77 min, M+H+=334; 1H NMR (CDCl3, 300 MHz): 8.35 (s, 1H), 7.62 (d, J=2.7 Hz, 1H), 7.45 (d, J=2.7 Hz, 1H), 7.38 (dt, J=8.2, 6.2 Hz, 1H), 7.22 (ddd, J=8.2, 2.3, 0.9 Hz, 1H), 7.15 (dt, J=9.9, 2.3 Hz, 1H), 6.98 (tdd, J=8.2, 2.3, 0.9 Hz, 1H), 4.52 (br. s, 1H), 4.31 (q, J=7.1 Hz, 2H), 3.94 (br. s, 1H), 1.37 (t, J=7.1 Hz, 3H), 1.22 (d, J=6.5 Hz, 6H).

Sources & evidence

ORD record: ord-b0fc9d0e5bc44c6093f661d19d6b3748
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410279B2

Reaction notes

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