Benzyl isocyanate → HCID 67267925, compound

HRID 251751Notes

Reaction equation

HRID 251751 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH3:8][NH:9][C:10](=[O:47])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:32]1[NH:33][C:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[CH:35][NH+:36]=1)[NH:17][C:18](C1CCCN(C2C=CC=CN=2)C1)=[O:19].CCN(C(C)C)C(C)C.[CH2:57]([N:64]=C=O)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH2:57]([NH:64][C:18]([NH:17][C@H:16]([C:32]1[NH:33][C:34]([C:37]2[CH:46]=[CH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=2)=[CH:35][NH+:36]=1)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([NH:9][CH3:8])=[O:47])=[O:19])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

5

Reactant 3

HCID 76639Benzyl isocyanateHCID 81531DiisopropylethylamineHCID 67268637HCID 67268637, compound

Product 1

HCID 67267925HCID 67267925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The amine from Example 327, BB2 (1 eq.) was dissolved in DCM, then DIPEA (1 eq.) and benzyl isocyanate were added. After stirring for 1 hr at RT the solvent were removed under reduced pressure and the crude was purified by preparative RP-HPLC, using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents (column: C18). The desired fractions were lyophilized to afford the titled compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.36 (1H, s), 8.16 (1H, s), 8.07 (1H, d, J=8.6 Hz), 8.02-7.93 (2H, m), 7.91 (1H, dd, J=8.6 Hz, J2=1.5 Hz), 7.71-7.55 (3H, m), 7.35-7.19 (5H, m), 6.75-6.67 (2H, m), 4.97-4.87 (1H, m), 4.30-4.15 (2H, m), 2.53 (3H, d, J=4.6 Hz), 2.04 (2H, t, J=7.4 Hz), 1.97-1.83 (2H, m), 1.55-1.44 (2H, m), 1.42-1.22 (4H, m). MS (ES) C29H33N5O2 requires: 483, found: 484 (M+H)+.

Workup

  1. customwere removed under reduced pressure
  2. customthe crude was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-6f60236b09514441bde45c897329a36b
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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