Diisopropylethylamine → 7-Methoxy-3-{1-[6-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepine-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 74697Notes

Reaction equation

HRID 74697 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](O)=[O:25])C=CN=4)[CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[S:30]1[C:39]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34][C:33]=2[N:32]=[CH:31]1.CCN(C(C)C)C(C)C.C[N:50]([C:52](ON1N=NC2C=CC=CC1=2)=[N+:53](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[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[CH2:13][CH2:14][N:15]([C:18]4[CH:23]=[C:22]([C:24]([N:36]5[CH2:37][CH2:38][C:39]6[S:30][CH:31]=[N:32][C:33]=6[CH2:34][CH2:35]5)=[O:25])[N:53]=[CH:52][N:50]=4)[CH2:16][CH2:17]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 226207475,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepineHCID 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 426132257-Methoxy-3-{1-[6-(4,5,7,8-tetrahydro-thiazolo[4,5-d]azepine-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

83 mg (0.21 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 37 mg (0.24 mmol) 5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine in 0.13 mL (0.72 mmol) DIPEA and 1.0 mL DMF were combined 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 and freeze-dried.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. customfreeze-dried

Sources & evidence

ORD record
ord-04cb521a323140b88fd061c0a255a304
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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