Formic Acid → 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-2'-carboxylic acid

HRID 74606Notes

Reaction equation

HRID 74606 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][NH:17][CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1.Br[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([C:28]([OH:30])=[O:29])[CH:23]=1.C(O)=O>CN1C(=O)CCC1>[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:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]([OH:30])=[O:29])[CH:23]=4)[CH2:16][CH2:15]3)[CH2:9][CH2:8][C:7]=2[CH:20]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7351504-Bromopyridine-2-carboxylic acidHCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one

Product 1

HCID 583864784-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-2'-carboxylic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7.0 g (25 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 2.5 g (12 mmol) 4-bromopicolinic acid in 25 mL NMP were stirred for 2 h at 110° C. The reaction mixture was combined with some formic acid and purified by preparative HPLC-MS. The product-containing fractions were combined and evaporated down. The residue was stirred with MeOH, suction filtered and dried.

Workup

  1. custompurified by preparative HPLC-MS
  2. customevaporated down
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-efd2dc8f86b144b6af130e801eebb32b
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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