Triethylamine → HCID 42610361, compound

HRID 2111317Notes

Reaction equation

HRID 2111317 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9](=[O:12])[N:8]([CH3:13])[C:7]3[CH:14]=[N:15][C:16]([NH:18][C:19]4[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][C:20]=4[O:28][CH3:29])=[N:17][C:6]2=3)[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.[NH2:54][CH:55]1[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]1.C(N(CC)CC)C>ClCCl>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9](=[O:12])[N:8]([CH3:13])[C:7]3[CH:14]=[N:15][C:16]([NH:18][C:19]4[CH:27]=[CH:26][C:22]([C:23]([NH:54][CH:55]5[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]5)=[O:25])=[CH:21][C:20]=4[O:28][CH3:29])=[N:17][C:6]2=3)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27375314-Amino-1-methylpiperidineHCID 57635006HCID 57635006, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 42610361HCID 42610361, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.059 g (0.00015 mole) of 4-(9-cyclobutyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid (I-23), 0.07 g (0.000185 mole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.05 mL (0.0004 mole) of 4-amino-1-methylpiperidine, 0.1 mL of triethylamine and 3 mL of dichloromethane was stirred for 2.5 hours at ambient temperature. The mixture was concentrated under reduced pressure and the residue purified by C18 reverse phase silica gel chromatography, eluting with an acetonitrile-water gradient (10:90-100:0) to give 0.018 g of 4-(9-cyclobutyl-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-24).

Workup

  1. concentrationThe mixture was concentrated 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-9389081d2a744c579e4ddd5b595db80d
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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