Acetonitrile → HCID 59657317, compound

HRID 353762Notes

Reaction equation

HRID 353762 reaction equation
[CH3:1][N:2]([CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][NH2:5].C(#N)C.[CH3:20][N:21]([CH3:76])[C@H:22]1[CH2:73][C@@H:72]([CH3:74])[O:71][CH:24]([O:25][C@@H:26]2[C@@H:42]([CH3:43])[C:41](=[O:44])[C@@H:40]([CH3:45])[C:39](=[O:46])[O:38][C@H:37]([CH2:47][CH3:48])[C@:36]3([CH2:49][CH3:50])[C@H:32](N(CCCCN4C5C(=NC=CC=5)N=C4)[C:34](=[O:51])[O:35]3)[C@@H:31]([CH3:65])[C:30](=[O:66])[C@H:29]([CH3:67])[CH2:28][C@@:27]2([O:69][CH3:70])[CH3:68])[C@@H:23]1[OH:75]>O>[CH3:76][N:21]([CH3:20])[C@H:22]1[CH2:73][C@@H:72]([CH3:74])[O:71][CH:24]([O:25][C@@H:26]2[C@@H:42]([CH3:43])[C:41](=[O:44])[C@@H:40]([CH3:45])[C:39](=[O:46])[O:38][C@H:37]([CH2:47][CH3:48])[C@:36]3([CH2:49][CH3:50])[C@H:32]([N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH2:6][C:7]4[C:16]5[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=5)[N:10]=[CH:9][CH:8]=4)[C:34](=[O:51])[O:35]3)[C@@H:31]([CH3:65])[C:30](=[O:66])[C@H:29]([CH3:67])[CH2:28][C@@:27]2([O:69][CH3:70])[CH3:68])[C@@H:23]1[OH:75]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 23511392HCID 23511392, compoundHCID 59657219HCID 59657219, compound

Product 1

HCID 59657317HCID 59657317, compoundYield 18%

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-Methyl-N1-quinolin-4-ylmethyl-ethane-1,2-diamine (6 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-tetra-oxotetradecahydro-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)-3a,4-diethyl-11-methoxy-7,9,11,13,15-pentamethyl-1-{2-[methyl-(quinolin-4-ylmethyl)amino]ethyl}-2,6,8,14-tetraoxotetradecahydro-2H-oxacyclotetradecino[4,3-d][1,3]oxazol-10-yl 3,4,6-trideoxy-3-(dimethylamino)-D-xylo-hexopyranoside (18% yield) as an off white solid. MH+(825.50).

Workup

  1. customThe reaction conditions

Sources & evidence

ORD record
ord-cf0210424c254a0eb1694a36e9566fee
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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