4-Fluoroaniline → HCID 67347260, compound

HRID 1676273Notes

Reaction equation

HRID 1676273 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][C:5]#[C:6][C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19](C)[CH:18]=2)[CH:8]=1)[CH3:2].FC1C=CC([NH:34][C:35]([C:37]2([C:40]([OH:42])=O)[CH2:39][CH2:38]2)=[O:36])=CC=1.[C:43]1(C(O)=O)(C(O)=O)CC1.[F:52][C:53]1[CH:59]=[CH:58][C:56](N)=[CH:55][CH:54]=1>>[CH2:25]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]#[C:6][C:7]1[S:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][C:13]=2[O:16][C:17]2[CH:18]=[CH:19][C:20]([N:23]([C:56]3[CH:58]=[CH:59][C:53]([F:52])=[CH:54][CH:55]=3)[C:40]([C:37]3([C:35]([NH2:34])=[O:36])[CH2:38][CH2:39]3)=[O:42])=[CH:21][C:22]=2[CH3:43])[CH:8]=1)[CH3:26]

Participants

5

Reactant 4

HCID 97314-FluoroanilineHCID 690171,1-Cyclopropanedicarboxylic acidHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidHCID 67347436HCID 67347436, compound

Product 1

HCID 67347260HCID 67347260, compound

Procedure

Prepared from 4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-2-methylbenzenamine (50 mg, 0.14 mmol), and 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (46 mg, 0.21 mmol; prepared from cyclopropane-1,1-dicarboxylic acid and 4-fluoroaniline using the methods described in WO 2005/030140 and by Shih and Rankin, Synth. Comm. 1996, 26(4), 833-836) according to the procedure for Example 74. The crude was purified by preparative TLC eluting with EtOAc/MeOH (9:1). The product was a light yellow oil (0.8 mg, 1%). 1H NMR (CDCl3, 400 MHz) δ 9.21 (s, 1H), 8.70 (s, 1H), 8.45 (d, J=5.5 Hz, 1H), 7.57 (s, 1H), 7.48 (m, 4H), 7.06 (m, 3H), 6.41 (d, J=5.5 Hz, 1H), 3.71 (s, 2H), 2.65 (q, J=7, 14 Hz, 4H), 2.17 (s, 3H), 1.71 (m, 4H), 1.13 (t, J=7.0 Hz, 6H). LRMS (APCI pos) m/e 571 (M+1).

Workup

  1. customThe crude was purified by preparative TLC
  2. washeluting with EtOAc/MeOH (9:1)

Sources & evidence

ORD record
ord-e9a7ec1b681c407681cc8582f6d772dc
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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