Methanol → HCID 86610039, compound

HRID 1433123Notes

Reaction equation

HRID 1433123 reaction equation
[C@@H:1]1([N:9]2[C:13]3[N:14]=[N:15][N:16]=[C:17]([N:18]=CN(C)C)[C:12]=3[N:11]=[CH:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.CO[CH:25](OC)[N:26]([CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:27][CH:28]([CH3:30])[CH3:29].C(Cl)Cl.CO.CO>O>[C@@H:1]1([N:9]2[C:13]3[N:14]=[N:15][N:16]=[C:17]([N:18]=[CH:25][N:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:31][CH:32]([CH3:33])[CH3:34])[C:12]=3[N:11]=[CH:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 109656001-Propanamine, N-(dimethoxymethyl)-2-methyl-N-(2-methylpropyl)-HCID 21226129Dichloromethane methanolHCID 86610040HCID 86610040, compound

Product 1

HCID 86610039HCID 86610039, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

As described for 9a but using N,N-di-isobutylformamide dimethylacetal. Colorless crystals (72%). M.p. 138-140°C. TLC (silica gel, CH2Cl2-MeOH, 9:1): Rf 0.40. UV (10% MeOH in water): λmax 236 (10100), 325 nm (25850). 1H-NMR ([D6]DMSO): δ 0.88, 0.94 (2d, 12 H, CH3); 1.95, 2.20 (2m, 2H, CH); 2.80 (2m, 2H, H2—C(2′)); 3.30-3.74 (m, 6H, H2—C(5′) and 2 CH2); 4.00 (m, 1H, H—C(4′)); 4.45 (m, 1H, H—C(3′)); 5.03 (t, 1H, 3J(H,H)=4.9 Hz, 5′—OH); 5.37 (d, 1H, 3J(H,H)=4.0 Hz, 3′—OH); 6.54 (t, 1H, 3J(H,H)=6.4 Hz, H—C(1′)); 8.78 (s, 1H, N═CH); 9.10 (s, 1H, H—C(8)). Anal. calcd. for C18H29N7O3. 1/2 H2O (400.5): C, 53.99; H 7.55; N 24.48; found: C 53.65; H 7.62; N 24.11.

Sources & evidence

ORD record
ord-87083f12e45f491a98684853254f149a
Source dataset
uspto-grants-2009_11
Patent number
US07612187B2

Reaction notes

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