Tert-butyl 3-oxopiperidine-1-carboxylate → HCID 53258406, compound

HRID 1921988Notes

Reaction equation

HRID 1921988 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[C:4]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH3:21])[N:15]=2)[CH:3]=1.O=[C:23]1[CH2:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]1>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]=[C:4]([C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH3:21])[N:15]=1)[CH:3]=[C:2]2[NH:1][CH:23]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1

Participants

3

Reactant 2

HCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 583363954-(4-amino-6-methoxynaphthalen-2-yl)-N-methylpyrimidin-2-amine

Product 1

HCID 53258406HCID 53258406, compound

Procedure

4-(6-methoxy-4-(piperidin-3-ylamino)naphthalen-2-yl)-N-methylpyrimidin-2-amine 152 was synthesized according to General Procedure E except compound 33 was used a starting material and replacing tert-butyl 4-oxopiperidine-1-carboxylate with tert-butyl 3-oxopiperidine-1-carboxylate. 1H NMR (DMSO) 400 MHz δ 9.64 (bs, 1H), 9.42 (bs, 1H), 8.42 (d, J=6.0 Hz, 1H), 8.20 (s, 1H), 7.92 (d, J=8.8 Hz, 1H), 7.81-7.70 (m, 2H), 7.47 (bs, 1H), 7.24 (dd, JA=8.8 Hz, JB=2.0 Hz, 1H), 4.24-4.16 (m, 1H), 3.98 (s, 3H), 3.51-3.44 (m, 1H), 3.29-3.22 (m, 1H), 3.09 (bs, 3H), 3.00-2.87 (m, 2H), 2.13-2.05 (m, 1H), 2.05-1.94 (m, 1H), 1.93-1.76 (m, 2H); LCMS: 364 [M+H]. Calc. for C21H25N5O 3.1 Hydrochloric Acid 0.85 Dichloromethane 0.4 Ethyl Acetate: C, 51.45; H, 5.89; N, 12.79; Found C 51.58, H 5.71, N 12.79.

Sources & evidence

ORD record
ord-c76a184d67f74b60b3bdc22dd9d525ae
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

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