Dimethylamine → HCID 178483118, compound

HRID 1591066Notes

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.[CH3:30][NH:31][CH3:32]>>[CH3:28][C:14]1([CH3:27])[C@@H:13]([OH:29])[C@H:12]([NH:11][C:5]2[C:4]([N:31]([CH3:32])[CH3:30])=[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:24])([F:25])[F:26])[CH:20]=2)[O:15]1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 178467515HCID 178467515, compound

Product 1

HCID 178483118HCID 178483118, compound

Procedure

In a method similar to Example 3, the product of Example 1, Step 2 (0.250 g, 0.572) was converted to the title compound with dimethylamine gas to give, after recrystallization from diethyl ether/hexane, 0.19 g (76%) of product as a white solid: mp 135°-140° C.; 1H NMR (DMSO-D6): δ 8.09 (br s, 1H), 7.23 (br s, 1H), 7.10 (d, 1H), 6.82 (d, 1H), 5.84 (br s, 1H), 4.77 (m, 1H), 3.75 (m, 1H), 3.35 (s, 3H), 2.53 (s, 3H), 1.38 (s, 3H), 1.19 (s, 3H); IR (KBr): 3400, 1600 cm-1 ; MS (m/z) 437 (MH+, 100%), 419 (65), 245 (35) 177 (70); [α]D25 = -85.4 (THF).

Sources & evidence

ORD record: ord-73197a675c16469d851179f882153547
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05206252

Reaction notes

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