Methyl D-prolinate hydrochloride → (R)-Methyl 1-[4-((3-(Sulfamoylmethyl)phenyl)amino)-1,3,5-triazin-2-yl]pyrrolidine-2-carboxylate

HRID 587154Notes

Reaction equation

HRID 587154 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1C[CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]([CH2:23][S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[N:11]=1.ClC1N=CN=C(NC2C=C(CS(N)(=O)=[O:44])C=CC=2)N=1.Cl.COC(=O)[C@H]1CCCN1>>[S:24]([CH2:23][C:19]1[CH:18]=[C:17]([NH:16][C:12]2[N:13]=[CH:14][N:15]=[C:10]([N:5]3[CH2:6][CH2:7][CH2:8][C@@H:4]3[C:3]([O:2][CH3:1])=[O:44])[N:11]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:26])(=[O:25])[NH2:27]

Participants

4

Reactant 3

HCID 44629857Methyl D-prolinate hydrochlorideHCID 60197106rac-3-[(4-(2-Methoxymethylpiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamideHCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Product 1

HCID 60197308(R)-Methyl 1-[4-((3-(Sulfamoylmethyl)phenyl)amino)-1,3,5-triazin-2-yl]pyrrolidine-2-carboxylate

Procedure

B21 was obtained as a white crystalline solid by following the procedure reported for B4 using A1 and (R)-proline methyl ester hydrochloride; yield: 158 mg (45%). 1H NMR (300 MHz, d6-DMSO, 300K) δ 1.88-2.08 (m, 3H), 2.22-2.42 (m, 1H), 3.50-3.77 (m, 2H), 3.55 and 3.60 (2 s, 3H), 4.22 (2 s, 2H), 4.50-4.67 (m, 1H), 6.88 (bs, 2H), 6.97-7.05 (m, 1H), 7.20-7.32 (m, 1H), 7.60-7.72 (m, 1H), 7.68 and 7.89 (2bs, 1H), 8.19 and 8.26 (2 s, 1H), 9.73 and 9.78 (2 s, 1H). MS (ES) C16H20N6O4S requires: 392. found: 393 (M+H)+.

Workup

  1. customB21 was obtained as a white crystalline solid

Sources & evidence

ORD record
ord-857639f1a6184e3fa22044fc6bcaf277
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

Loading…