Acetonitrile → HCID 59657297, compound

HRID 353763Notes

Reaction equation

HRID 353763 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][N:8]([CH3:12])[CH2:9][CH2:10][NH2:11])[CH:4]=[C:3]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:2]=1.C(#N)C.[CH3:22][N:23]([CH3:78])[C@H:24]1[CH2:75][C@@H:74]([CH3:76])[O:73][CH:26]([O:27][C@@H:28]2[C@@H:44]([CH3:45])[C:43](=[O:46])[C@@H:42]([CH3:47])[C:41](=[O:48])[O:40][C@H:39]([CH2:49][CH3:50])[C@:38]3([CH2:51][CH3:52])[C@H:34](N(CCCCN4C5C(=NC=CC=5)N=C4)[C:36](=[O:53])[O:37]3)[C@@H:33]([CH3:67])[C:32](=[O:68])[C@H:31]([CH3:69])[CH2:30][C@@:29]2([O:71][CH3:72])[CH3:70])[C@@H:25]1[OH:77]>O>[CH3:78][N:23]([CH3:22])[C@H:24]1[CH2:75][C@@H:74]([CH3:76])[O:73][CH:26]([O:27][C@@H:28]2[C@@H:44]([CH3:45])[C:43](=[O:46])[C@@H:42]([CH3:47])[C:41](=[O:48])[O:40][C@H:39]([CH2:49][CH3:50])[C@:38]3([CH2:51][CH3:52])[C@H:34]([N:11]([CH2:10][CH2:9][N:8]([CH2:7][C:5]4[CH:4]=[C:3]([C:13]5[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=5)[CH:2]=[N:1][CH:6]=4)[CH3:12])[C:36](=[O:53])[O:37]3)[C@@H:33]([CH3:67])[C:32](=[O:68])[C@H:31]([CH3:69])[CH2:30][C@@:29]2([O:71][CH3:72])[CH3:70])[C@@H:25]1[OH:77]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11507001HCID 11507001, compoundHCID 59657219HCID 59657219, compound

Product 1

HCID 59657297HCID 59657297, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

C12 ethyl, C9, C10, C11 enone, 3 oxo, C12 OCOIm macrolide of Example 11 (1 eq) was added to N1-[3,3′]Bipyridinyl-5-ylmethyl-N1-methyl-ethane-1,2-diamine (3 eq), acetonitrile, and water (10%). The reaction conditions are the same as described previously for (3aS,4R,7R,9R,10R,11S,13R,15R,15aR)-3a,4-diethyl-1-[4-(1H-imidazo[4,5-b]pyridin-1-yl)butyl]-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside, yielding (3aS,4R,7R,9R,10R,11S,13R,15R,15aR)-1-{2-[(3,3′-bipyridin-5-ylmethyl)(methyl)amino]ethyl }-3a,4-diethyl-11-methoxy-7,9,11,13,15-pentamethyl-2,6,8,14-tetraoxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside (27% yield) as a white solid. MH+(852.50).

Workup

  1. customThe reaction conditions

Sources & evidence

ORD record
ord-76b4d48c93e84df68107f0a829f9c122
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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