Hydrochloric Acid → (2-[(E)-3-[1-(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester

HRID 1176733Notes

Reaction equation

HRID 1176733 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[C:29]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH2:43])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C(Cl)CCl.CN(C=O)C>[C:32]([O:31][C:29](=[O:30])[NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH:43][C:17](=[O:19])/[CH:16]=[CH:15]/[C:12]1[CH:13]=[CH:14][N:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:20])=[CH:6][CH:5]=2)(=[O:8])=[O:9])[CH:11]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 66646287(E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid2×

Product 1

HCID 86613977(2-[(E)-3-[1-(toluene-4-sulfonyl)-1-H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

Starting materials: (E)-3-[1-(toluene-4-sulfonyl)-1H-pyrrol-3yl]-acrylic acid (compound A1) (0.400 g), HOBtH2O (0.285 g), triethylamine (652 μl), DMF (25 ml), EDC?HCl (0.698 g), N—BOC-1,2-phenylenediamine (0.286 g). Reaction conditions: room temperature, 1 hour; room temperature, 2 hours.

Workup

  1. customReaction conditions
  2. customroom temperature, 1 hour
  3. customroom temperature, 2 hours

Sources & evidence

ORD record
ord-161a8ed6be6e442994fc45f02ad5a1ce
Source dataset
uspto-grants-2010_11
Patent number
US07842820B2

Reaction notes

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