Trifluoroacetic acid → HCID 10006445, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=2)[N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[N:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=[CH:37][C:36]=1[CH:45]=O.[B][B][B][B][B][B][B][B][B][B].C(O)(C(F)(F)F)=O>>[CH2:31]([N:30]([CH2:33][CH3:34])[C:28](=[O:29])[C:25]1[CH:24]=[CH:23][C:22]([C@@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:45][C:36]3[CH:37]=[CH:38][C:39]4[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:35]=3)[CH:3]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:27][CH:26]=1)[CH3:32]Participants
Procedure
Using the same method as for COMPOUND 17 and using INTERMEDIATE 5a (209 mg, 0.45 mmol), 2-quinolinecarboxaldehyde (77.6 mg, 0.49 mmol), and decaborane (16.4 mg, 0.13 mmol) afforded COMPOUND 54 (162 mg, 38% yield) as its TFA salt. This material was lyophilized from CH3CN/H2O to produce a yellow solid. Purity (HPLC): >98%; Optical purity (Chiral HPLC): >99%; 1H NMR (400 MHz, CD3OD) δ 1.07 (br t, J=6.7 Hz, 3H), 1.23 (br t, J=6.6 Hz, 3H), 2.59 (br s, 4H), 3.18 (br t, J=4.4 Hz, 6H), 3.52 (br q, J=7.2 Hz, 2H), 4.30 (s, 1H), 4.89 (s, 2H), 6.58 (dd, J=7.9, 2.1 Hz, 1H), 6.72 (s, 1H), 6.82 (d, J=7.4 Hz, 1H), 7.04-7.12 (m, 3H), 7.36 (d, J=8.2 Hz, 2H), 7.85-7.93 (m, 2H), 8.09 (td, J=7.8, 1.2 Hz, 1H), 8.22 (d, J=8.2 Hz, 1H), 8.27 (d, J=8.4 Hz, 1H), 8.87 (d, J=8.6 Hz, 1H). Found: C, 50.15; H, 4.57; N, 7.46. C32H37N5O×1.1 H2O×3.6 CF3COOH has C, 50.20; H, 4.60; N, 7.47%. [α]D17=+20.8 deg [c 0.726, MeOH].
Sources & evidence
- ORD record
- ord-8042086b655243fc8f066846cedd1a13
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07241764B2
Reaction notes
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