Piperidine → HCID 44548771, compound

HRID 1676618Notes

Reaction equation

HRID 1676618 reaction equation
C1C2C(COC(=O)[NH:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:52])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30]4[N:31]=[CH:32][C:33]5[N:39]([CH3:40])[C:38](=[O:41])[C:37]([F:43])([F:42])[CH2:36][N:35]([CH:44]6[CH2:48][CH2:47][CH2:46][CH2:45]6)[C:34]=5[N:49]=4)=[C:25]([O:50][CH3:51])[CH:24]=3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>ClCCl>[NH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:52])[C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]2[N:31]=[CH:32][C:33]3[N:39]([CH3:40])[C:38](=[O:41])[C:37]([F:42])([F:43])[CH2:36][N:35]([CH:44]4[CH2:48][CH2:47][CH2:46][CH2:45]4)[C:34]=3[N:49]=2)=[C:25]([O:50][CH3:51])[CH:24]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 44548770HCID 44548770, compound

Product 1

HCID 44548771HCID 44548771, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the suspension 0.12 g (0.16 mmole) of {3-[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]-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester (I-73) in 2 mL of dichloromethane was added 0.4 mL of piperidine. The mixture was stirred at room temperature for 1 hour, then volatiles were removed under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-methanol (gradient, 100:0-0:100) gave 0.027 g of N-(3-amino-propyl)-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-benzamide (I-74) as a white solid.

Workup

  1. customvolatiles were removed under reduced pressure
  2. customPurification by silica gel chromatography
  3. washeluting with dichloromethane-methanol (gradient, 100:0-0:100)

Sources & evidence

ORD record
ord-c9e0ce06a5c040eba08eeb22cef03a08
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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