1,2-Dichloroethane → HCID 89455778, compound

HRID 1776458Notes

Reaction equation

HRID 1776458 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][C@H:7]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28][CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH:19]=1)[CH2:8][C:9]1[C:14]([Cl:15])=[CH:13][N+:12]([O-:16])=[CH:11][C:10]=1[Cl:17])=[O:5].[C:33]([O:37][C:38]([N:40]([C:45]1[CH:46]=[C:47]([CH:51]=[CH:52][C:53]=1[O:54][CH2:55][CH:56]1[CH2:58][CH2:57]1)C(O)=O)[S:41]([CH3:44])(=[O:43])=[O:42])=[O:39])([CH3:36])([CH3:35])[CH3:34].C(Cl)CCl.CN([CH:66]=[O:67])C>CN(C1C=CN=CC=1)C.Cl>[C:33]([O:37][C:38]([N:40]([C:45]1[CH:46]=[CH:47][C:51]([C:66]([NH:2][CH2:3][C:4]([O:6][C@H:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([F:27])[F:26])=[C:20]([O:28][CH2:29][CH:30]3[CH2:32][CH2:31]3)[CH:19]=2)[CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][N+:12]([O-:16])=[CH:11][C:10]=2[Cl:17])=[O:5])=[O:67])=[CH:52][C:53]=1[O:54][CH2:55][CH:56]1[CH2:57][CH2:58]1)[S:41]([CH3:44])(=[O:42])=[O:43])=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 86679413HCID 86679413, compoundHCID 90194457HCID 90194457, compound

Product 1

HCID 89455778HCID 89455778, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolvent

Procedure

((S)-4-(2-(2-aminoacetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)ethyl)-3,5-dichloropyridine 1-oxide hydrochloride) (103 mg; 0.2 mmol) was dissolved in DMF (1.5 ml), then 3-(N-(tert-butoxycarbonyl)methylsulfonamido)-4-(cyclopropylmethoxy)benzoic acid (80 mg, 0.2 mmol), (for a reference procedure see Example 18, WO 2010/089107, which is incorporated herein by reference in its entirety), EDC (80 mg, 0.42 mmol), and DMAP (60 mg, 0.49 mmol) were added. The reaction was stirred at RT overnight, then was diluted with HCl 1M and extracted with EtOAc. The organic phase was washed with HCl 1M and with K2CO3 sat, dried over Na2SO4 and evaporated under vacuum to give 180 mg of the desired product (Yield: quantitative).

Workup

  1. additionwere added
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with HCl 1M and with K2CO3
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-f3b63050877446fcab8d8fffcf5a1426
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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