Dichloromethane → HCID 17987997, compound

HRID 1982933Notes

Reaction equation

HRID 1982933 reaction equation
[NH2:1][C:2]1C(Cl)=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.Cl.CN(C)[CH2:17][CH2:18][CH2:19][N:20]=[C:21]=NCC.Cl.[C:27]([C:31]1[CH:32]=[C:33]([NH:43][C:44]([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49](CC3CCNCC3)[CH:48]=2)=[O:45])[N:34]([C:36]2[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=2)[N:35]=1)([CH3:30])([CH3:29])[CH3:28].[CH2:60]([Cl:62])Cl>>[NH2:1][C:2]1[C:60]([Cl:62])=[CH:9][C:5]([C:6]([N:20]2[CH:21]3[CH2:17][CH2:18][CH:19]2[CH2:4][CH:5]([CH2:9][C:50]2[CH:51]=[CH:52][C:47]([NH:46][C:44]([NH:43][C:33]4[N:34]([C:36]5[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=5)[N:35]=[C:31]([C:27]([CH3:30])([CH3:28])[CH3:29])[CH:32]=4)=[O:45])=[CH:48][CH:49]=2)[CH2:6]3)=[O:8])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17987852HCID 17987852, compound

Product 1

HCID 17987997HCID 17987997, compound

Procedure

4-amino-5-chloro-2-methoxybenzoic acid (60 mg, 0.30 mmol) is dissolved in DCM and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (64 mg, 0.30 mmol) is added followed by the addition of Intermediate 3 (130 mg, 0.28 mmol). The reaction is stirred at room temperature for overnight and the reaction is concentrated to dryness and purified on a 10 gram silica gel column using ethyl acetate/heptane (35%/65%) to give 60 mg of 1-{4-[8-(4-Amino-5-chloro-2-methoxy-benzoyl)-8-aza-bicyclo[3.2.1]oct-3-ylmethyl]-phenyl}-3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-urea, Compound A1441, Example 6. m/z(LCMS) M+1=636, RT=3.47 minutes.

Workup

  1. concentrationthe reaction is concentrated to dryness
  2. custompurified on a 10 gram silica gel column

Sources & evidence

ORD record
ord-54a78e9e194d499ea1797907a655db36
Source dataset
uspto-grants-2009_06
Patent number
US07541368B2

Reaction notes

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