Cis tert-Butyl 4-aminocyclohexylcarbamate → HCID 66818969, compound

HRID 1024782Notes

Reaction equation

HRID 1024782 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:34]=[C:33]([F:35])[C:13]([O:14][C:15]2[CH:16]=[C:17]([CH:21]=[C:22]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=3)[CH:23]=2)[C:18](O)=[O:19])=[C:12]([F:36])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:37]([O:41][C:42](=[O:51])[NH:43][CH:44]1[CH2:49][CH2:48][CH:47]([NH2:50])[CH2:46][CH2:45]1)([CH3:40])([CH3:39])[CH3:38]>>[C:37]([O:41][C:42](=[O:51])[NH:43][CH:44]1[CH2:45][CH2:46][CH:47]([NH:50][C:18](=[O:19])[C:17]2[CH:21]=[C:22]([O:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=3)[CH:23]=[C:15]([O:14][C:13]3[C:12]([F:36])=[CH:11][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:34][C:33]=3[F:35])[CH:16]=2)[CH2:48][CH2:49]1)([CH3:40])([CH3:38])[CH3:39]

Participants

3

Reactant 2

HCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 66818640HCID 66818640, compound

Product 1

HCID 66818969HCID 66818969, compoundYield 48.1%

Procedure

3-[4-(tert-butoxycarbonylamino-methyl)-2,6-difluoro-phenoxy]-5-(4-cyano-phenoxy)-benzoic acid (0.6 g, 1.2 mmol) and (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (0.28 g, 1.3 mmol) and other reagents as described in Example 9(e) were used to afford 0.4 g of the required product. 1H NMR (DMSO-d6): δ 1.24 (4H, m), 1.42 (18H, s), 1.8 (4H, m), 3.18 (1H, m), 3.64 (1H, m), 4.20 (2H, d), 6.74 (1H, d), 7.0 (1H, s), 7.16 (4H, m), 7.24 (1H, s), 7.38 (1H, s), 7.54 (1H, t), 7.88 (2H, d), 36 (1H, d).

Sources & evidence

ORD record
ord-3c51748ab85f425fb431e47ccd4b1cf0
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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