O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 3-{-[6-(5-hydroxymethyl-4.7-dihydro-5H-thieno[2,3-c]pyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 74692Notes

Reaction equation

HRID 74692 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[NH:7][C:8](=[O:27])[N:9]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[C:22]([C:24]([OH:26])=O)C=[CH:20][N:19]=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[S:30]1[C:34]2[CH2:35][NH:36][CH:37]([CH2:39][OH:40])[CH2:38][C:33]=2[CH:32]=[CH:31]1.C[N:42](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[OH:40][CH2:39][CH:37]1[N:36]([C:24]([C:22]2[N:42]=[CH:20][N:19]=[C:18]([N:15]3[CH2:16][CH2:17][CH:12]([N:9]4[CH2:10][CH2:11][C:5]5[CH:4]=[C:3]([O:2][CH3:1])[CH:29]=[CH:28][C:6]=5[NH:7][C:8]4=[O:27])[CH2:13][CH2:14]3)[CH:23]=2)=[O:26])[CH2:35][C:34]2[S:30][CH:31]=[CH:32][C:33]=2[CH2:38]1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 23465912(4,5,6,7-Tetrahydrothieno[2,3-c]pyridin-5-yl)methanolHCID 583864334-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4'-carboxylic acid

Product 1

HCID 426131453-{-[6-(5-hydroxymethyl-4.7-dihydro-5H-thieno[2,3-c]pyridin-6-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

100 mg (0.25 mmol) 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4′-carboxylic acid and 50 mg (0.28 mmol) (4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-5-yl)-methanol in 50 μL (0.36 mmol) TEA and 0.90 mL DMF were combined with 85 mg (0.27 mmol) TBTU and the mixture was stirred for 5 h at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and evaporated down roughly by half. The precipitate formed was suction filtered and dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. customevaporated down roughly by half
  3. customThe precipitate formed
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-b5f2f3b98bf54a6b9be45a2b4fd17b22
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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