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Hydrochloric Acid → HCID 9891181, compound

HRID 2108681
Notes
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Reaction equation

HRID 2108681 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][N:3]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[NH2:26].Cl.C(OCC)C>CC(O)C>[ClH:1].[N+:18]([C:5]1[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[O:12])=[N:7][C:2]([NH:26][C:25]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:23]([O:22][CH3:21])[CH:24]=2)=[N:3][CH:4]=1)([O-:20])=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 322853,4,5-TrimethoxyanilineHCID 57632411HCID 57632411, compound

Product 1

HCID 9891181HCID 9891181, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-[(2-chloro-5-nitropyrimidin-4-yl)amino]benzamide (52 mg, 0.178 mmol) and 3,4,5-trimethoxyaniline (34 mg, 0.185 mmol) in 2-propanol (2 mL) was added 1N HCl in diethyl ether (50 uL, 0.05 mmol). The reaction mixture was heated at 90° C. for approx. 18 hours. After the reaction was cooled to room temperature cold diethyl ether was added to precipitate out the product. The precipitate was filtered and washed with cold diethyl ether, then dried under vacuum to give 2-({5-nitro-2-[(3,4,5-trimethoxyphenyl)amino]pyrimidin-4-yl}amino)benzamide hydrochloride (30 mg, 35%) as a dark brown solid. 1H NMR (DMSO-d6/D2O): δ 9.07 (s, 1H), 8.26 (m, 1 H), 7.69 (d, 1 H), 7.34 (t, 1 H), 7.19 (t, 1 H), 6.92 (s, 2 H), 3.77 (s, 3 H), 3.59 (s, 6 H). MS m/z 440 (M+1).

Workup

  1. additionwas added
  2. customto precipitate out the product
  3. filtrationThe precipitate was filtered
  4. washwashed with cold diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-701723b5e80544ea9407e202e7c6c552
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07514446B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes