Diisopropylethylamine → HCID 67058689, compound

HRID 470327Notes

Reaction equation

HRID 470327 reaction equation
N[C:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][N:4]([C:10]2[N:19]=[CH:18][C:17]3[CH2:16][CH2:15][C:14]4[CH:20]=[C:21](OC)[CH:22]=[CH:23][C:13]=4[C:12]=3[N:11]=2)[N:3]=1.C([N:29](C(C)C)CC)(C)C.[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=2)[CH2:38][CH2:37]1.CN([C:54]([O:58]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([NH:50][C:7]([C:6]3[CH:2]=[N:3][N:4]([C:10]4[N:19]=[CH:18][C:17]5[CH2:16][CH2:15][C:14]6[C:20]([O:58][CH3:54])=[CH:21][CH:22]=[CH:23][C:13]=6[C:12]=5[N:11]=4)[C:5]=3[NH2:29])=[O:9])=[CH:48][CH:49]=2)[CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 242554804-[2-(4-Methylpiperazin-1-yl)ethyl]anilineHCID 59784811HCID 59784811, compound

Product 1

HCID 67058689HCID 67058689, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-Amino-1-(8-methoxy-5,6-dihydro-benzo[h]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid (40 mg, 0.118 mM), diisopropylethylamine (70 ul, 0.402 mM), 4-[2-(4-Methyl-piperazin-1-yl)-ethyl]-phenylamine (30 mg, 0.1369 mM) in DMF (1 ml) to which was added HBTU (60 mg, 0.1583 mM) and the stirred 16 hr at room temperature. The resulting suspension was filtered and the solid washed with water (1×1 ml) and dried in vacuo to afford 5-Amino-1-(7-methoxy-5,6-dihydro-benzo[h]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid {4-[2-(4-methyl-piperazin-1-yl)-ethyl]-phenyl}-amide (12 mg, 19% yield) as a white solid. ES-MS MH+ 539. The filtrate may be purified via RP-HPLC 0.1% TFA to afford additional material.

Workup

  1. customthe stirred 16 hr
  2. customat room temperature
  3. filtrationThe resulting suspension was filtered
  4. washthe solid washed with water (1×1 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-343dbc835ae347d492100b37bbd99117
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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