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

HRID 1176734Notes

Reaction equation

HRID 1176734 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](O)=[O:18])=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[C:37]([NH:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[NH2:51])([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>C(Cl)CCl.CN(C=O)C.C(N(CC)CC)C.O>[C:40]([O:39][C:37](=[O:38])[NH:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[NH:51][C:17](=[O:18])/[CH:16]=[CH:15]/[C:12]1[CH:13]=[CH:14][N:10]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH:11]=1)([CH3:43])([CH3:42])[CH3:41]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 66646147(E)-3-[1-(biphenyl-4-sulfonyl)-1H-pyrrol-3-yl]-acrylic acid2×

Product 1

HCID 86613978(2-{(E)-3-[1-(biphenyl-4-sulfonyl)-1H-pyrrol-3-yl]-allanoylamino}-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Starting materials: (E)-3-[1-(biphenyl-4-sulfonyl)-1H-pyrrol-3-yl)-acrylic acid (compound B2) (0.300 g), HOBt?H2O (0.130 g), triethylamine (668 μl), DMF (20 ml), EDC?HCl (0.508 g), N—BOC-1,2-phenylenediamine (0.176 g). Reaction conditions: room temperature, 1 hour; room temperature, 17 hours.

Workup

  1. customReaction conditions
  2. customroom temperature, 1 hour
  3. customroom temperature, 17 hours

Sources & evidence

ORD record
ord-dc8e92f3971d47e4a8a9bbcbc5d469e8
Source dataset
uspto-grants-2010_11
Patent number
US07842820B2

Reaction notes

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