1-Hydroxybenzotriazole → HCID 49842493, compound

HRID 1615776Notes

Reaction equation

HRID 1615776 reaction equation
C(OC([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[N:11]([CH2:22][C:23](O)=[O:24])[C:10](=[O:26])[CH:9]1[CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=O)(C)(C)C.[NH2:33][C:34]1[CH:35]=[C:36]2[C:49](=[CH:50][CH:51]=1)[CH2:48][C@:38]1([C:46]3[C:41](=[N:42][CH:43]=[CH:44][CH:45]=3)[NH:40][C:39]1=[O:47])[CH2:37]2.Cl.C(N=C=NCCCN(C)C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:20][C:18]1[CH:19]=[C:14]([CH:12]2[N:11]([CH2:22][C:23]([NH:33][C:34]3[CH:35]=[C:36]4[C:49](=[CH:50][CH:51]=3)[CH2:48][C@:38]3([C:46]5[C:41](=[N:42][CH:43]=[CH:44][CH:45]=5)[NH:40][C:39]3=[O:47])[CH2:37]4)=[O:24])[C:10](=[O:26])[CH:9]([CH:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[NH:8][CH2:13]2)[CH:15]=[C:16]([F:21])[CH:17]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53260812(R)-5-Amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-oneHCID 68154283HCID 68154283, compound2×

Product 1

HCID 49842493HCID 49842493, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.10 g (0.22 mmol) 2-(4-(tert-butoxycarbonyl)-6-(3,5-difluorophenyl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)piperazin-1-yl)ethanoic acid (isomer mixture 1.1.1), 60 mg (0.24 mmol) (R)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, 58 mg (0.30 mmol) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-hydrochloride, 41 mg (0.30 mmol) HOBT, 0.03 ml (0.24 mmol) TEA and 1.5 ml DMF were stirred overnight at RT. The reaction mixture was concentrated by rotary evaporation. The residue was stirred with 15 ml of a 1.25M methanolic hydrochloric acid solution for 1 h at 50° C. The mixture was concentrated by rotary evaporation and the residue was purified by HPLC. The product-containing fractions were combined and lyophilised. The product was obtained as an isomer mixture.

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. concentrationThe mixture was concentrated by rotary evaporation
  3. customthe residue was purified by HPLC
  4. customThe product was obtained as an isomer mixture

Sources & evidence

ORD record
ord-33b64d7feb264360ad54f882652b8c33
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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