Pyrrolidine → HCID 178431215, compound

HRID 1591069Notes

Reaction equation

C(O[C:4]1[C:5]([NH:11][C@@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][C:23]([F:26])([F:25])[F:24])[CH:20]=3)[O:15][C:14]([CH3:28])([CH3:27])[C@H:13]2[OH:29])=[N:6][S:7](=[O:10])(=[O:9])[N:8]=1)C.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH3:27][C:14]1([CH3:28])[C@@H:13]([OH:29])[C@H:12]([NH:11][C:5]2[C:4]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[N:8][S:7](=[O:10])(=[O:9])[N:6]=2)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][C:23]([F:25])([F:26])[F:24])[CH:20]=2)[O:15]1

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 178467515HCID 178467515, compound

Product 1

HCID 178431215HCID 178431215, compound

Procedure

In a method similar to Example 5, the product of Example 1, Step 2 (0.218 g, 0.500 mmol) was converted to the title compound with pyrrolidine (0.053 g, 0.780 mmol) in 1 hour to give 0.34 g of product which was purified by flash column (3:2 hexane/ethyl acetate) to afford 0.17 (74%) of white solid after recrystallization: mp 243°-245° C.; 1H NMR (DMSO-D6): δ 7.74 (d, 1H), 7.29 (d, 1H), 7.18 (dd, 1H), 6.89 (d, 1H), 5.81 (d, 1H), 4.94 (t, 1H), 4.00 (m, 1H), 3.87 (m, 2H), 3.57 (m, 2H), 2.10-1.90 (m, 4H), 1.41 (s, 3H), 1.17 (s, 3H); IR (KBr): 3350, 1595 cm-1 ; MS (m/z) 463 (MH +, 100%); [α]D25 =-75.5 (THF).

Sources & evidence

ORD record: ord-65fc3ed1141f45cba12538f94e4c0264
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05206252

Reaction notes

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