Pyrrolidine → HCID 178467155, compound

HRID 526136Notes

Reaction equation

HRID 526136 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21](Cl)[N:22]=3)[N:17]=[CH:16][C:15]=2[C:25](=[O:27])[CH3:26])[CH2:9][CH2:8]1)(=O)=O.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[N:28]1([C:21]2[N:22]=[C:23]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:25](=[O:27])[CH3:26])=[C:14]3[NH:13][C@H:10]2[CH2:11][CH2:12][C@H:7]([CH2:6][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH2:8][CH2:9]2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 117773884HCID 117773884, compound

Product 1

HCID 178467155HCID 178467155, compoundYield 33.6%

Procedure

Following general procedure V, {4-[(3-acetyl-6-chloro-1,5-naphthyridin-4-yl)amino]-cyclohexyl}methyl methanesulfonate (180 mg, 0.437 mmol) was reacted with pyrrolidine (34 mg, 0.48 mmol) to afford the desired product (34 mg, 18%) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 8.63 (s, 1H), 7.83 (d, J=9.2 Hz, 1H), 7.02 (d, J=9.2 Hz, 1H), 5.57 (br s, 1H), 3.61-3.53 (m, 4H), 2.63 (s, 6H), 2.45 (d, J=7.0 Hz, 2H), 2.30-2.18 (m, 2H), 2.14-2.04 (m, 4H), 1.98-1.91 (m, 2H), 1.89-1.80 (m, 4H), 1.68-1.55 (m, 1H), 1.40-1.28 (m, 2H), 1.18-1.08 (m, 2H); ESI MS m/z 422 [M+H]+; HPLC 97.5% (AUC), tR=9.68 min.

Sources & evidence

ORD record
ord-060c68b7b6844455921911de11968696
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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