Diisopropylethylamine → 7-Chloro-3-{1-[6-(2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 74632Notes

Reaction equation

HRID 74632 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[N:9]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1.Cl[C:21]1[N:26]=[CH:25][N:24]=[C:23]([C:27]([N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH2:30]2)=[O:28])[CH:22]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[N:9]([CH:13]3[CH2:14][CH2:15][N:16]([C:21]4[CH:22]=[C:23]([C:27]([N:29]5[C:37]6[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=6)[CH2:31][CH2:30]5)=[O:28])[N:24]=[CH:25][N:26]=4)[CH2:17][CH2:18]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58117518(6-Chloropyrimidin-4-yl)-(2,3-dihydroindol-1-yl)-methanoneHCID 581811547-Chloro-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Product 1

HCID 583866007-Chloro-3-{1-[6-(2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

110 mg (0.36 mmol) 7-chloro-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one were added to 87.6 mg (0.34 mmol) (6-chloropyrimidin-4-yl)-(2,3-dihydro-indol-1-yl)-methanone and 63 μL (0.37 mmol) DIPEA in 2.5 mL DMF. The reaction mixture was stirred overnight at RT, then concentrated by rotary evaporation using the rotary evaporator and purified by preparative HPLC. The corresponding product fractions were combined and evaporated down using the rotary evaporator. The residue was taken up in DMF and combined with methanol. The substance was precipitated, suction filtered, washed with a little methanol and dried.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. customthe rotary evaporator
  3. custompurified by preparative HPLC
  4. customevaporated
  5. customthe rotary evaporator
  6. customThe substance was precipitated
  7. filtrationsuction filtered
  8. washwashed with a little methanol
  9. customdried

Sources & evidence

ORD record
ord-bc1ea1f4e44541759ba3a56e079a6620
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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