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Diisopropylethylamine → 6-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acidmethoxy-methyl-amide

HRID 469371
Notes
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Reaction equation

HRID 469371 reaction equation
[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[CH:11]=[C:10](Cl)[N:9]=[CH:8][N:7]=1)=[O:5].[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]2[NH:25][C:24](=[O:26])[N:23]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH2:22][CH2:21][C:20]=2[CH:33]=1.CCN(C(C)C)C(C)C>C1COCC1.O>[CH3:1][O:2][N:3]([CH3:13])[C:4]([C:6]1[CH:11]=[C:10]([N:30]2[CH2:29][CH2:28][CH:27]([N:23]3[CH2:22][CH2:21][C:20]4[CH:33]=[C:16]([O:15][CH3:14])[CH:17]=[CH:18][C:19]=4[NH:25][C:24]3=[O:26])[CH2:32][CH2:31]2)[N:9]=[CH:8][N:7]=1)=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 581812166-Chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amide

Product 1

HCID 581811336-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acidmethoxy-methyl-amide

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

0.20 g (0.99 mmol) 6-chloro-pyrimidine-4-carboxylic acidmethoxy-methyl-amide, 0.28 g 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 0.20 mL (1.16 mmol) DIPEA in 1.5 mL THF were heated to 120° C. in the microwave for 30 min. The mixture was diluted with water and extracted with DCM. The combined organic phases were dried on sodium sulphate, filtered and evaporated down i. vac. The residue was triturated with diethyl ether, suction filtered and dried.

Workup

  1. extractionextracted with DCM
  2. customThe combined organic phases were dried on sodium sulphate
  3. filtrationfiltered
  4. customevaporated down i
  5. customThe residue was triturated with diethyl ether, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-3236cce6c4b142b195a693cfeb07c18e
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08629137B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes