Diisopropylethylamine → HCID 178485854, compound

HRID 416388Notes

Reaction equation

HRID 416388 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:35])[O:14][CH2:15][C@@H:16]([N:21]([CH3:34])[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[Cl:33])=[O:23])[CH2:17][CH2:18][CH2:19][NH2:20])=[CH:5]2.[CH:36]1[CH:41]=[CH:40][C:39]([O:42][C:43](OC2C=CC=CC=2)=[N:44][C:45]#[N:46])=[CH:38][CH:37]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([NH:12][C:13](=[O:35])[O:14][CH2:15][C@@H:16]([N:21]([CH3:34])[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[Cl:33])=[O:23])[CH2:17][CH2:18][CH2:19][NH:20]/[C:43](=[N:44]/[C:45]#[N:46])/[O:42][C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1)=[CH:5]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 57947596HCID 57947596, compound

Product 1

HCID 178485854HCID 178485854, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (S)-5-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)pentyl 6-fluoroisoquinolin-3-ylcarbamate (190 mg, 0.35 mmol) and diphenyl cyanocarbonimidate (83 mg, 0.35 mmol) in DCM (10.0 mL) was added DIEA (0.12 mL, 0.70 mmol). The reaction mixture was stirred at RT for 4 h. The mixture was concentrated under reduced pressure to give (S,Z)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-((cyanoimino)(phenoxy)methylamino)pentyl 6-fluoroisoquinolin-3-ylcarbamate, which was used without further purification. LRMS (M+H+) m/z 650.2.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52987fe28c564598a8f5cf79e49add6e
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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