Toluene → 3-(1-cyanocyclopropyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)phenyl]benzamide

HRID 2190492Notes

Reaction equation

HRID 2190492 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4]1)#[N:2].S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[NH2:26][C:27]1[CH:28]=[C:29]([CH:46]=[CH:47][CH:48]=1)[O:30][C:31]1[CH:45]=[CH:44][C:34]2[N:35]=[C:36]([NH:38][C:39]([CH:41]3[CH2:43][CH2:42]3)=[O:40])[O:37][C:33]=2[CH:32]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([NH:26][C:27]2[CH:48]=[CH:47][CH:46]=[C:29]([O:30][C:31]3[CH:45]=[CH:44][C:34]4[N:35]=[C:36]([NH:38][C:39]([CH:41]5[CH2:42][CH2:43]5)=[O:40])[O:37][C:33]=4[CH:32]=3)[CH:28]=2)=[O:11])[CH2:4][CH2:5]1)#[N:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 574410393-(1-Cyanocyclopropyl)benzoic acidHCID 67312021N-[6-(3-aminophenoxy)-1,3-benzooxazol-2-yl]cyclopropanecarboxamide

Product 1

HCID 583490613-(1-cyanocyclopropyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)phenyl]benzamideYield 66.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using 3-(1-cyanocyclopropyl)benzoic acid (224 mg, 1.19 mmol), thionyl chloride (1 mL, 13.7 mmol), toluene (5 mL), N-[6-(3-aminophenoxy)-1,3-benzooxazol-2-yl]cyclopropanecarboxamide (131 mg, 424 μmol) produced in Example B1(vii), pyridine (5 mL), and N,N-dimethylpyridine-4-amine (28.1 mg, 230 μmol) as starting materials, and in the same manner as in Example B1(viii), the title compound (135 mg, 66%) was obtained as a colorless solid.

Sources & evidence

ORD record
ord-daba385beaff4230a367145f2a3c6286
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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