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Methylamine → HCID 178485040, compound

HRID 2189951
Notes
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Reaction equation

HRID 2189951 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:9]([C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]=[C:7]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:6]1.C(N(CC)CC)C.C1C=CC(O[C:44](OC2C=CC=CC=2)=[N:45][C:46]#[N:47])=CC=1.[CH3:55][NH2:56]>CC(O)C.CO>[C:55](/[N:47]=[C:46](/[NH:45][CH3:44])\[NH:1][CH2:2][CH2:3][CH2:4][C:5]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:9]([C:10](=[O:15])[C:11]([CH3:14])([CH3:12])[CH3:13])[N:8]=[C:7]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:6]1)#[N:56]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 601398321-(2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 178485040HCID 178485040, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

1-(2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-2,2-dimethylpropan-1-one (66 mg, 0.158 mmol) was weighed into a flask, then dissolved in 2.0 mL IPA. Triethylamine (0.055 ml, 0.38 mmol) was then added followed by diphenyl cyanocarbonimidate (75 mg, 0.316 mmol). The reaction was then stirred at room temperature for 1.5 hours. The reaction was then transferred to a scaled tube, followed by addition of 3 mL of methyl amine (2.4 ml, 4.9 mmol) in MeOH. The reaction was then placed in a 60° C. bath for 12 hours. The reaction vas then removed and concentrated, and the residue was purified by flash column chromatography (3-7% MeOH/CH2Cl2) to provide the desired product (32 mg, 41%) as a light orange foam film. MS ESI (+) m/z 499 (M+E) detected; 1H NMR (400 MHz, MeOH) δ 7.48 (m, 1H), 7.44 (d, J=8.0 Hz, 2H), 7.38 (m, 2H), 7.28 (m, 3H), 3.45 (m, 1H), 3.39 (m, 1H), 3.27 (m, 1H), 2.78 (s, 3H), 2.45 (m, 1H), 1.99 (m, 1H), 1.59 (m, 1H), 1.39 (s, 9H).

Workup

  1. customThe reaction was then transferred to a scaled tube
  2. customwas then placed in a 60° C.
  3. customfor 12 hours
  4. customThe reaction vas
  5. customthen removed
  6. concentrationconcentrated
  7. customthe residue was purified by flash column chromatography (3-7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0df3a7af2aa440b2818ce5d312c24598
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324257B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes