Triethylamine → HCID 57635048, compound

HRID 2111370Notes

Reaction equation

HRID 2111370 reaction equation
[CH:1]1([N:6]2[CH2:12][CH:11]([CH2:13][CH2:14][OH:15])[C:10](=[O:16])[N:9]([CH3:17])[C:8]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.[NH2:58][CH:59]1[CH2:64][CH2:63][N:62]([CH3:65])[CH2:61][CH2:60]1.C(N(CC)CC)C>ClCCl>[CH:1]1([N:6]2[CH2:12][CH:11]([CH2:13][CH2:14][OH:15])[C:10](=[O:16])[N:9]([CH3:17])[C:8]3[CH:18]=[N:19][C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([NH:58][CH:59]5[CH2:64][CH2:63][N:62]([CH3:65])[CH2:61][CH2:60]5)=[O:28])=[CH:25][C:24]=4[O:32][CH3:33])=[N:21][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27375314-Amino-1-methylpiperidineHCID 68902731HCID 68902731, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 57635048HCID 57635048, compoundYield 143.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.047 g (0.0001 mole) of (rac)-4-[9-cyclopentyl-7-(2-hydroxy-ethyl)-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino]-3-methoxy-benzoic acid (I-49a), 0.043 g (0.00011 mole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.027 g (0.000023 mole) of 4-amino-1-methylpiperidine, 0.05 mL of triethylamine and 2 mL of dichloromethane was stirred at room temperature for 1.5 hours and then concentrated under reduced pressure. The residue purified by C18 reverse phase silica gel chromatography, eluting with an acetonitrile-water gradient (10:90-100:0) to give 0.0182 g of (rac)-4-[9-cyclopentyl-7-(2-hydroxy-ethyl)-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino]-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (I-49)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue purified by C18 reverse phase silica gel chromatography
  3. washeluting with an acetonitrile-water gradient (10:90-100:0)

Sources & evidence

ORD record
ord-a81974d6da694f32a4938f9d6ca09cd3
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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