Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylate → methyl 4-amino-1-(2'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazoline]-4'-yl)piperidine-4-carboxylate

HRID 2059753Notes

Reaction equation

HRID 2059753 reaction equation
C(OC([NH:8][C:9]1([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=O)(C)(C)C.CC1C=CC(S(O[C:30]2[C:39]3[CH2:38][CH2:37][CH2:36][C:35]4([CH2:43][CH2:42][CH2:41][CH2:40]4)[C:34]=3[N:33]=[C:32]([NH2:44])[N:31]=2)(=O)=O)=CC=1>>[NH2:8][C:9]1([C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:11][N:12]([C:30]2[C:39]3[CH2:38][CH2:37][CH2:36][C:35]4([CH2:43][CH2:42][CH2:41][CH2:40]4)[C:34]=3[N:33]=[C:32]([NH2:44])[N:31]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 14537079Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylateHCID 866343332'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazolin]-4'-yl 4-methylbenzenesulfonate

Product 1

HCID 44231854methyl 4-amino-1-(2'-amino-6',7'-dihydro-5'H-spiro[cyclopentane-1,8'-quinazoline]-4'-yl)piperidine-4-carboxylate

Procedure

The title product was prepared using the procedures outlined in Examples 1G and 1H, substituting methyl 4-(tert-butoxycarbonylamino)piperidine-4-carboxylate (CAS# 115655-44-2) for the product from Example 1D. 1H NMR (300 MHz, CDCl3) δ 4.50 (s, 2 H), 3.74 (s, 3 H), 3.30-3.36 (m, 4 H), 2.45 (t, J=4.58 Hz, 2 H), 2.04-2.21 (m, 4 H), 1.79-1.92 (m, J=4.07 Hz, 2 H), 1.49-1.73 (m, 10 H). MS (DCI+) m/z 360 (M+H).

Sources & evidence

ORD record
ord-63f64f524da94b9ab0c8443e3a825a39
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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