Methanol → HCID 178481548, compound

HRID 81193Notes

Reaction equation

HRID 81193 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:28][C@H:29]4[CH2:34][CH2:33][C@H:32]([CH3:35])[CH2:31][CH2:30]4)[C:15]([N:17]4[CH2:22][C:21](=[O:23])[N:20]([CH3:24])[C@H:19]5[CH2:25][CH2:26][CH2:27][C@H:18]45)=[N:16][C:12]=3[CH:11]=[C:10]([C:36](=[N:38][OH:39])[NH2:37])[N:9]=2)[CH:5]=[N:6][CH:7]=1.[CH3:40][OH:41]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]([CH2:28][C@H:29]4[CH2:34][CH2:33][C@H:32]([CH3:35])[CH2:31][CH2:30]4)[C:15]([N:17]4[CH2:22][C:21](=[O:23])[N:20]([CH3:24])[C@H:19]5[CH2:25][CH2:26][CH2:27][C@H:18]45)=[N:16][C:12]=3[CH:11]=[C:10]([C:36]3[NH:37][C:40](=[O:41])[O:39][N:38]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 178481550HCID 178481550, compound

Product 1

HCID 178481548HCID 178481548, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4aS,7aS)-4-[4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-3H-imidazo[4,5-c]pyridin-2-yl]-1-methyloctahydro-2H-cyclopenta[b]pyrazin-2-one was prepared in analogy to Example 3.1, Step 3 using 4-(5-chloropyridin-3-yl)-N′-hydroxy-3-[(trans-4-methylcyclohexyl)methyl]-2-[(4aS,7aS)-4-methyl-3-oxooctahydro-1H-cyclopenta[b]pyrazin-1-yl]-3H-imidazo[4,5-c]pyridine-6-carboximidamide (197 mg, 0.357 mmol) as starting material and 0-20% methanol in DCM as eluant for chromatography. MS ESI calc'd. for C29H33ClN8O3 [M+H]+ 577. found 577. 1H NMR (500 MHz, DMSO-d6) δ 12.89 (s, 1H), 8.98 (d, J=2.0 Hz, 1H), 8.81 (d, J=2.0 Hz, 1H), 8.49 (t, J=2.0 Hz, 1H), 8.04 (s, 1H), 4.31-4.28 (m, 1H), 3.88-3.84 (m, 2H), 3.69-3.61 (m, 3H), 2.88 (s, 3H), 2.34-2.24 (m, 1H), 2.31-2.04 (m, 1H), 1.89-1.75 (m, 2H), 1.70-1.61 (m, 1H), 1.47-1.33 (m, 3H), 1.25-1.20 (m, 2H), 1.08-0.98 (m, 1H), 0.85-0.82 (m, 1H), 0.73-0.60 (m, 5H), 0.62-0.33 (m, 2H).

Sources & evidence

ORD record
ord-603d494b72d9499db253671e7afdf8db
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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