[8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester → N1-[5-(4-Trifluoromethylphenyl)oxazol-2-yl]-5,6,7,8-tetrahydronaphthalene-1,7-diamine

HRID 1785574

Reaction equation

HRID 1785574 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([NH:18][C:19]3[O:20][C:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[CH:22][N:23]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:9]1)(C)(C)C.C(OC(=O)NC1CCC2C(=C(NC3OC(C4C=CC(C)=CC=4)=CN=3)C=CC=2)C1)(C)(C)C>>[F:33][C:30]([F:31])([F:32])[C:27]1[CH:28]=[CH:29][C:24]([C:21]2[O:20][C:19]([NH:18][C:11]3[C:10]4[CH2:9][CH:8]([NH2:7])[CH2:17][CH2:16][C:15]=4[CH:14]=[CH:13][CH:12]=3)=[N:23][CH:22]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 67229286[8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl esterHCID 67229897{8-[5-(4-Trifluoromethylphenyl)oxazol-2-ylamino]-1,2,3,4-tetrahydro-naphthalen-2-yl}carbamic acid tert-butyl ester

Product 1

HCID 11964241N1-[5-(4-Trifluoromethylphenyl)oxazol-2-yl]-5,6,7,8-tetrahydronaphthalene-1,7-diamineYield 38.1%

Procedure

The title compound was prepared using the procedure as described in Example 20H substituting the product of Example 21A (120 mg, 0.253 mmol) for the product of Example 20G. The crude product was purified by trituration with Et2O/hexanes which resulted in 36 mg (38%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 9.32 (br s, 1H), 7.75 (m, 4H), 7.60 (s, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.10 (t, J=7.8 Hz, 1H), 6.87 (d, J=7.8 Hz, 1H), 3.05-2.70 (m, 4H), 2.30 (m, 1H), 1.82 (m, 3H), 1.43 (m, 1H); MS (ESI+) m/z 374 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified by trituration with Et2O/hexanes which

Sources & evidence

ORD record
ord-821a060f8c434154a296276dd9d3588a
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Linked notes

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