1,2,3,4-Tetrahydropyrrolo(1,2-a)pyrazine → 3-{1-[6-(3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 74701Notes

Reaction equation

HRID 74701 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]4[N:25]=[CH:24][N:23]=[C:22]([C:26](O)=[O:27])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:29]=1.[CH2:30]1[NH:35][CH2:34][CH2:33][N:32]2[CH:36]=[CH:37][CH:38]=[C:31]12.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:30]1[N:35]([C:26]([C:22]2[N:23]=[CH:24][N:25]=[C:20]([N:17]3[CH2:18][CH2:19][CH:14]([N:10]4[CH2:9][CH2:8][C:7]5[CH:29]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=5[NH:12][C:11]4=[O:13])[CH2:15][CH2:16]3)[CH:21]=2)=[O:27])[CH2:34][CH2:33][N:32]2[CH:36]=[CH:37][CH:38]=[C:31]12

Participants

5

Reactant 3

HCID 15491281,2,3,4-Tetrahydropyrrolo(1,2-a)pyrazineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 583866166-[4-(7-Methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Product 1

HCID 426133033-{1-[6-(3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

83 mg (0.21 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid and 37 mg (0.24 mmol) 1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrazine in 0.10 mL (0.72 mmol) TEA and 2.0 mL DMF were mixed with 77 mg (0.24 mmol) TBTU and the mixture was stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined, the acetonitrile was evaporated down and the residue was dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. customthe acetonitrile was evaporated down
  3. customthe residue was dried

Sources & evidence

ORD record
ord-eb4e7e9ec5ad4add8ac7ffc32ceb4281
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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