tert-butyl N-(3-bromopropyl)carbamate → HCID 66818759, compound

HRID 1024721Notes

Reaction equation

HRID 1024721 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][C:6]([O:7][C:8]2[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:22]=2)[C:11]([NH:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:12])=[CH:5][CH:4]=1)#[N:2].[C:34]([O:38][C:39](=[O:45])[NH:40][CH2:41][CH2:42][CH2:43]Br)([CH3:37])([CH3:36])[CH3:35]>>[C:34]([O:38][C:39](=[O:45])[NH:40][CH2:41][CH2:42][CH2:43][N:17]1[CH2:16][CH2:15][CH:14]([NH:13][C:11](=[O:12])[C:10]2[CH:20]=[C:21]([O:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=3)[CH:22]=[C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:33][CH:32]=3)[CH:9]=2)[CH2:19][CH2:18]1)([CH3:37])([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 66818786HCID 66818786, compound

Product 1

HCID 66818759HCID 66818759, compoundYield 85%

Procedure

Following procedure of Example 11(e) 3,5-bis-(4-cyano-phenoxy)-N-piperidin-4-yl-benzamide 0.35 g (0.79 mmol) and (3-bromo-propyl)-carbamic acid tert-butyl ester (0.188 g, 0.79 mmol) were used to afford 0.4 g of the required product. 1H NMR (DMSO-d6): δ 1.38 (9H, s), 1.52 (4H, m), 1.75 (2H, m), 1.90 (2H, m), 2.28 (2H, m), 2.82 (1H, m), 2.92 (2H, m), 3.74 (1H, brs), 3.68 (1H, m), 6.79 (1H, brs), 7.18 (1H, t), 7.26 (4H, d), 7.52 (2H, s), 7.88 (4H, d), 8.38 (1H, d).

Sources & evidence

ORD record
ord-4600e5042c0142acaead24d04bfe5ec6
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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