Diisopropylethylamine → HCID 44548768, compound

HRID 1676615Notes

Reaction equation

HRID 1676615 reaction equation
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.Cl.[NH2:43][CH:44]1[CH2:49][CH2:48][N:47]([C:50]([O:52][CH2:53][CH:54]2[C:66]3[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:60]3[C:55]2=[CH:56][CH:57]=[CH:58][CH:59]=3)=[O:51])[CH2:46][CH2:45]1>CN(C)C=O>[CH:65]1[C:66]2[CH:54]([CH2:53][O:52][C:50]([N:47]3[CH2:48][CH2:49][CH:44]([NH:43][C:26](=[O:27])[C:25]4[CH:29]=[CH:30][C:22]([NH:21][C:19]5[N:18]=[CH:17][C:8]6[N:9]([CH3:16])[C:10](=[O:15])[C:11]([F:13])([F:14])[CH2:12][N:6]([CH:1]7[CH2:5][CH2:4][CH2:3][CH2:2]7)[C:7]=6[N:20]=5)=[C:23]([O:31][CH3:32])[CH:24]=4)[CH2:45][CH2:46]3)=[O:51])[C:55]3[C:60](=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:61]=2[CH:62]=[CH:63][CH:64]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27562294-Amino-1-N-Fmoc-piperidine hydrochlorideHCID 252529054-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

Product 1

HCID 44548768HCID 44548768, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.15 g (0.34 mmole) of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid (I-22), 0.24 mL (1.3 mmole) of ethyldiisopropyl amine and 0.13 g (0.37 mmole) of 4-amino-1-Fmoc-piperidine hydrochloride in 5.0 mL of dimethylformamide was added 0.16 g (0.37 mmole) of 1-(di-1-pyrrolidinylmethylene)-1H-benzotriazolium 3-oxide hexafluorophosphate. The mixture was stirred at room temperature for 1 hour, then diluted with 10 mL of ice water. The resulting solid was collected by filtration, washed with saturated sodium carbonate and water, and dried under vacuum to give 0.25 g of 4-[4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoylamino]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (I-70) as a white solid.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with saturated sodium carbonate and water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-c32f15349e394c0a92cdcdee87f0bb51
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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