Diisopropylethylamine → HCID 11591316, compound

HRID 1094158Notes

Reaction equation

HRID 1094158 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]2[C:18](=[CH:19][CH:20]=1)[CH2:17][C:7]1([C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]1=[O:16])[CH2:6]2.[O:21]=[C:22]1[N:26]2[CH2:27][C:28](=[O:34])[NH:29][C:30]3[CH:31]=[CH:32][CH:33]=[C:24]([C:25]=32)[N:23]1[CH2:35][C:36]([OH:38])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[O:21]=[C:22]1[N:26]2[CH2:27][C:28](=[O:34])[NH:29][C:30]3[CH:31]=[CH:32][CH:33]=[C:24]([C:25]=32)[N:23]1[CH2:35][C:36]([N:2]([CH3:1])[C:3]1[CH:4]=[C:5]2[C:18](=[CH:19][CH:20]=1)[CH2:17][C:7]1([C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]1=[O:16])[CH2:6]2)=[O:38]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 54776257HCID 54776257, compound2×HCID 59257892HCID 59257892, compound

Product 1

HCID 11591316HCID 11591316, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(methylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, enantiomer B (14 mg, 0.053 mmol, described in Intermediate 19), (2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)acetic acid (14 mg, 0.058 mmol, described in Intermediate 9), PyBOP (41 mg, 0.079 mmol), and N,N-diisopropylethylamine (0.028 mL, 0.158 mmol) was stirred in DMF (1 mL) at 50° C. for 20 h. The reaction mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The pure, product-containing fractions were combined and lyophilized to give the title compound. MS: m/z=495 (M+1). HRMS: m/z=495.1778; calculated m/z=495.1776 for C27H23N5O4.

Workup

  1. customThe reaction mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O
  3. additionThe pure, product-containing fractions

Sources & evidence

ORD record
ord-36597099f22445d782e83b964873d861
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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