Triethylamine → HCID 66830071, compound

HRID 1687229Notes

Reaction equation

HRID 1687229 reaction equation
[Cl:1][C:2]1[C:3]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34](=[O:37])[NH:35][CH3:36])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][N:17]([CH2:19][CH2:20][O:21]C(=O)C)[CH2:16][CH2:15][N:14]([CH3:25])[C:13]=3[CH:26]=2)=[N:6][CH:7]=1.ClC1C(NC2C=CC=CC=2C(NC)=O)=NC(NC2C=CC3CNCCN(C)C=3C=2)=NC=1.C(OCCBr)(=O)C.C(N(CC)CC)C>CO.ClCCl.CN(C=O)C>[Cl:1][C:2]1[C:3]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([NH:35][CH3:36])=[O:37])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][N:17]([CH2:19][CH2:20][OH:21])[CH2:16][CH2:15][N:14]([CH3:25])[C:13]=3[CH:26]=2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 135641-Acetoxy-2-bromoethaneHCID 66830031HCID 66830031, compoundHCID 67263792Acetic acid 2-{8-[5-chloro-4-(2-methylcarbamoyl-phenylamino)-pyrimidin-2-ylamino]-1-methyl-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-ethyl ester

Product 1

HCID 66830071HCID 66830071, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Synthesis of Acetic acid 2-{8-[5-chloro-4-(2-methylcarbamoyl-phenylamino)-pyrimidin-2-ylamino]-1-methyl-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl}-ethyl ester: To 40 ml sure-seal reaction vial, 2-[5-chloro-2-(1-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide (105 mg, 0.19 mmole), 2-bromoethyl acetate (36 mg, 0.21 mmole), triethylamine (0.3 ml, 2.1 mmoles), KI (10 mg, catalytic), and DMF (5 ml) were added. The reaction was heated to 700 C for 18 hours. The solvent was removed under vacuum to afford a brown solid. The desired product (10 mg, 10%) was isolated via column chromatography with dichloromethane and methanol as eluant. LCMS (ESI+) 524.42 (M+H)

Workup

  1. customTo 40 ml sure-seal
  2. customreaction vial
  3. temperatureThe reaction was heated to 700 C for 18 hours
  4. customThe solvent was removed under vacuum
  5. customto afford a brown solid

Sources & evidence

ORD record
ord-f385cbf6cfbb42b79d3652fca4fcacf4
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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