Isopropylamine → HCID 178457006, compound

HRID 1591068Notes

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.[CH:30]([NH2:33])([CH3:32])[CH3:31]>>[CH3:31][CH:30]([NH:33][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:24])([F:25])[F:26])[CH:20]=3)[O:15][C:14]([CH3:27])([CH3:28])[C@H:13]2[OH:29])=[N:6][S:7](=[O:9])(=[O:10])[N:8]=1)[CH3:32]

Participants

Reactant 2

HCID 6363Isopropylamine

HCID 178467515HCID 178467515, compound

Product 1

HCID 178457006HCID 178457006, compound

Procedure

In a method similar to Example 5, the product of Example 1, Step 2 (0.200 g, 0.457 mmol) was converted to the title compound with isopropylamine (0.64 mL, 7.5 mmol) in 1 hour to give 0.180 g (87%) of a white solid: mp 296-298 (dec); 1H NMR (DMSO-D6): δ 8.90 (br s, 1H), 8.30 (br s, 1H), 7.26 (s, 1H), 7.23 (d, 1H), 6.91 (d, 1H), 6.00 (d, 1H), 4.78 (d, 1H), 3.86 (br t, 1H), 3.63 (dd, 1H), 1.40 (s, 3H), 1.24 (dd, 6H), 1.16 (s, 3H); IR (KBr) 3300, 1620 cm-1 ; MS (m/z) 451 (MH+, 100%); [α]D25 =-73.5 (THF)

Sources & evidence

ORD record: ord-5a5b2939a8af499f93fec9646de44f35
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05206252

Reaction notes

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