1,1'-Carbonyldiimidazole → HCID 59586778, compound

HRID 218534Notes

Reaction equation

HRID 218534 reaction equation
[Si:1]([O:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]2[CH:31]=[CH:30][C:29]([NH:32][CH2:33][C@@H:34]([OH:45])[CH2:35][NH:36][C:37]([C:39]3[S:40][C:41]([Cl:44])=[CH:42][CH:43]=3)=[O:38])=[CH:28][C:27]=2[Cl:46])[C:21]1=[O:47])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:48](N1C=CN=C1)(N1C=CN=C1)=[O:49]>C(#N)CCC.CN(C)C1C=CN=CC=1>[Si:1]([O:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][N:22]([C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:33][C@H:34]([CH2:35][NH:36][C:37]([C:39]4[S:40][C:41]([Cl:44])=[CH:42][CH:43]=4)=[O:38])[O:45][C:48]3=[O:49])=[CH:28][C:27]=2[Cl:46])[C:21]1=[O:47])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59586714HCID 59586714, compound

Product 1

HCID 59586778HCID 59586778, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8008ButyronitrileSolvent

Procedure

A solution of 850 mg (1.196 mmol) of the compound from example 94A and 387 mg (2.39 mmol) of carbonyldiimidazole in 30 ml of butyronitrile is admixed with 3 mg (0.024 mmol) of 4-dimethylaminopyridine and heated to reflux. After 15 hours, the majority of the solvent is removed on a rotary evaporator. The product is isolated further by means of preparative HPLC with an acetonitrile/water mixture. This affords 605 mg (69% of theory) of the title compound.

Workup

  1. temperatureheated to reflux
  2. customthe majority of the solvent is removed on a rotary evaporator
  3. customThe product is isolated further by means of preparative HPLC with an acetonitrile/water mixture

Sources & evidence

ORD record
ord-dd0392ae324941f2a1f34a719798c371
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

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