Ethyl isocyanate → HCID 67030480, compound

HRID 1959979Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH2:26])=[C:8](C(OC(C)(C)C)=O)[N:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[CH2:27]([N:29]=[C:30]=[O:31])[CH3:28]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:26][C:30]([NH:29][CH2:27][CH3:28])=[O:31])=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([F:18])[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 8022Ethyl isocyanate

HCID 58271009HCID 58271009, compound

Product 1

HCID 67030480HCID 67030480, compoundYield 76%

Procedure

Following general method 4, employing 3-amino-1-(4-chloro-3-fluoro-phenyl)-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester and ethyl isocyanate, afforded the title compound as a yellow solid (0.65 g, 76%); LCMS (method B): RT=3.87 min, M+H+=354; 1H NMR (DMSO-D6, 400 MHz): 8.27 (s, 1H), 7.91 (d, J=2.7 Hz, 1H), 7.86 (dd, J=10.9, 2.6 Hz, 1H), 7.68-7.63 (m, 2H), 7.54-7.50 (m, 1H), 7.23 (t, J=5.3 Hz, 1H), 4.28 (q, J=7.1 Hz, 2H), 3.13-3.05 (m, 2H), 1.31 (t, J=7.1 Hz, 3H), 1.05 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record: ord-8c9afb1124924e0097d08b2d543740d8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410279B2

Reaction notes

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