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

HRID 1931045Notes

Reaction equation

HRID 1931045 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.CCN=C=NCCCN(C)C.Cl.[C:45]([NH:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH2:59])([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46]>CN(C=O)C.C(N(CC)CC)C.O>[C:48]([O:47][C:45](=[O:46])[NH:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][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)([CH3:51])([CH3:50])[CH3:49]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 3

HCID 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-1c63eae50fbd49c3830d8536b960aa86
Source dataset
uspto-grants-2012_05
Patent number
US08188138B2

Reaction notes

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