Ethyl isocyanate → HCID 67031346, compound

HRID 1959977Notes

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].[CH2:26]([N:28]=[C:29]=[O:30])[CH3:27]>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([NH:25][C:29]([NH:28][CH2:26][CH3:27])=[O:30])=[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 8022Ethyl isocyanate

HCID 58271024HCID 58271024, compound

Product 1

HCID 67031346HCID 67031346, compoundYield 73%

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 ethyl isocyanate, afforded the title compound as a cream solid (0.192 g, 73%); LCMS (method B): RT=3.61 min, M+H+=320; 1H NMR (CDCl3, 300 MHz): 8.41 (s, 1H), 7.62 (d, J=2.7 Hz, 1H), 7.44 (d, J=2.7 Hz, 1H), 7.38 (dt, J=8.2, 6.2 Hz, 1H), 7.21 (dd, J=8.2, 2.4 Hz, 1H), 7.14 (dt, J=9.9, 2.4 Hz, 1H), 6.98 (td, J=8.2, 2.4 Hz, 1H), 4.73 (s, 1H), 4.31 (q, J=7.1 Hz, 2H), 3.35-3.26 (m, 2H), 1.37 (t, J=7.1 Hz, 3H), 1.21 (t, J=7.1 Hz, 3H).

Sources & evidence

ORD record: ord-0b6a49099e894200b1e1a2cb0d86b6dd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410279B2

Reaction notes

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