Cyclopropylamine → HCID 470057, compound

HRID 1281656Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C@@H:5]1([N:14]2[C:18]3[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:17]=3[N:16]=[C:15]2Cl)[O:11][C@@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]1[OH:7]>>[CH:1]1([NH:4][C:15]2[N:14]([C@@H:5]3[O:11][C@@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]3[OH:7])[C:18]3[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:17]=3[N:16]=2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 470053HCID 470053, compound

Product 1

HCID 470057HCID 470057, compound

Procedure

The procedure is the same as that described for compound 7a, except that cyclopropylamine was used instead of isopropylamine, and compound 4a (300 mg, 0.80 mmoles) was used. Yield 299 mg (65%) as a white solid. Mp: 184-186° C. 1H NMR (DMSO-d6): δ7.47 (s, 1H), 7.36 (s, 1H), 7.05 (bs, 1H, D2O exchangeable), 5.72 (m, 1H), 5.24 (m, 1H, D2O exchangeable), 5.17 (m, 1H, D2O exchangeable), 4.65 (bs, 2H, D2O exchangeable), 4.53 (m, 1H), 4.42 (m, 1H), 4.15 (m, 1H), 3.66 and 3.57 (m, 2H), 0.86 (m, 2H), 0.57 (m, 1H), 0.50 (m, 1H). Anal. (C15H17O4N3Cl2) C, H, N.

Sources & evidence

ORD record: ord-145c9b9d0bc243adad5fb6f18482c71d
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455506B1

Reaction notes

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