4-Nitrobenzylamine → HCID 68422863, compound

HRID 1818918Notes

Reaction equation

HRID 1818918 reaction equation
[N:1]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[C:4]([C:10]([OH:12])=O)=[N:3][CH:2]=1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>ClCCl>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][C:10]([C:4]2[C:5]3[S:9][CH:8]=[CH:7][C:6]=3[N:1]=[CH:2][N:3]=2)=[O:12])=[CH:22][CH:23]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 291474-NitrobenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57415848Thieno[3,2-d]pyrimidine-4-carboxylic acid

Product 1

HCID 68422863HCID 68422863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 7.2 (1.0 mmol) and 4-nitrobenzyl amine (1.0 mmol) in dichloromethane (5.0 mL) is added TEA (3.0 equivalents) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (“HATU”; 1.1 equivalents). After completion of the reaction, the reaction is partitioned between EtOAc and water. The organic layer is separated, washed with 0.5 N HCl, saturated sodium bicarbonate, brine and dried. Purification by flash column chromatography on silica gel provides thieno[3,2-d]pyrimidine-4-carboxylic acid 4-nitro-benzylamide (compound 7.3).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction is partitioned between EtOAc and water
  3. customThe organic layer is separated
  4. washwashed with 0.5 N HCl, saturated sodium bicarbonate, brine
  5. customdried
  6. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-df74501d418c410a813a3ad76ba1b264
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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