2-Azabicyclo(2.2.1)hept-5-en-3-one → HCID 53820607, compound

HRID 1417010Notes

Reaction equation

HRID 1417010 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4](Cl)[N:3]=1.[NH2:13][C@H:14]1[CH2:18][C:17]([CH2:19][OH:20])=[CH:16][CH2:15]1.C12CC(C=C1)C(=O)N2>>[NH2:1][C:2]1[N:3]=[C:4]([NH:13][C@H:14]2[CH2:18][C:17]([CH2:19][OH:20])=[CH:16][CH2:15]2)[C:5]([NH:9][CH:10]=[O:11])=[C:6]([Cl:8])[N:7]=1

Participants

4

Reactant 3

HCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-oneHCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamideHCID 54043755HCID 54043755, compound

Product 1

HCID 53820607HCID 53820607, compound

Procedure

By the method of Example 7, N-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide (Example 3, 2.56 g, 52.4 mmol) was reacted with (4R)-4-amino-1-cyclopentene-1-methanol (1.4 g, 52.4 mmol), available from (-)-2-azabicyclo[2.2.1]hept-5-en-3-one (Chiroscience) by methods described in Examples 1-4 and 42 of U.S. Pat. No. 5,049,671. Crystallization from ethyl acetate-methanol gave title compound as white crystals, m.p. 148-150° C.; mass spectrum (Cl/CH4): 286, 284 (M+1), 190, 188 (B+H); 1H-NMR (DMSO-d6)δ: 8.97 and 8.55 (s and d with J=11.3 Hz total 1, NHCHO), 8.12 and 7.80 (s and d with J=11.5 Hz, total 1, CHO), 7.00 and 7.78 (both d, J=7.4 Hz, total 1, NH), 6.60 and 6.40 (both 8, total 2, NH2), 5.48 (s, 1, =CH), 4.74 (t, J=5.5 Hz, 1, OH), 4.74-4.60 (m, 1, NCH), 4.0-3.90 (m, 2, CH2O), 2.75-2.55 and 2.40-2.15 (both m, 2 each, 2CH2); [α]58920 -4.4°, [α]57820 -5.2°, [α]546 20 -4.8°, [α]43620 -20.0°, [α]365 20 -60.4° (c 0.25, methanol).

Workup

  1. customCrystallization from ethyl acetate-methanol

Sources & evidence

ORD record
ord-11086673cdf041b7a2efdc58bf1d909f
Source dataset
uspto-grants-1999_06
Patent number
US05917041

Reaction notes

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