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

HRID 870083Notes

Reaction equation

HRID 870083 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19](O)=[O:20])=[CH:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[C:34]([NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[NH2:48])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>C(Cl)CCl.CN(C=O)C.C(N(CC)CC)C.O>[C:37]([O:36][C:34](=[O:35])[NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[NH:48][C:19](=[O:20])/[CH:18]=[CH:17]/[C:14]1[CH:15]=[CH:16][N:12]([S:9]([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:22])=[CH:8][CH:7]=2)(=[O:11])=[O:10])[CH:13]=1)([CH3:40])([CH3:39])[CH3:38]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 66646380(E)-3-[1-(4-dimethylamino-benzenesulfonyl)-1H-pyrrol-3-yl)-acrylic acid2×

Product 1

HCID 86613979(2-[(E)-3-[1-(4-dimethylamino-benzenesulfonyl)-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-(4-dimethylamino-benzenesulfonyl)-1H-pyrrol-3-yl)-acrylic acid (compound B3) (0.150 g), HOBt?H2O (0.072 g), triethylamine (259 μl), DMF (10 ml), EDC?HCl (0.269 g), N-BOC-1,2-phenylenediamine (0.049 g). Reaction conditions: room temperature, 1 hour; room temperature, 21 hours.

Workup

  1. customReaction conditions
  2. customroom temperature, 1 hour
  3. customroom temperature, 21 hours

Sources & evidence

ORD record
ord-8a1b912f34294701a9f3e56dcbd49f19
Source dataset
uspto-grants-2015_03
Patent number
US08969401B2

Reaction notes

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