Dimethylformamide → HCID 136387748, compound

HRID 1924388Notes

Reaction equation

HRID 1924388 reaction equation
[CH2:1]([C:3]1[C:4]2[C:27]3=[CH:28][C:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]4[O:37][C:15]([NH:16][C@@H:17]([CH:34]([CH3:36])[CH3:35])[C:18](=[O:33])[N:19]5[CH2:29][C@H:22]([O:23][C:24]3=[N:25][CH:26]=1)[CH2:21][C@H:20]5[C:30](O)=[O:31])=[N:14][N:13]=4)=[CH:6][CH:5]=2)[CH3:2].Cl.N[C@]1(C(NN[S:49]([CH:52]2[CH2:54][CH2:53]2)(=[O:51])=[O:50])=O)C[C@@H]1CC.CCN(C(C)C)C(C)C.CN(C(O[N:72]1N=[N:79][C:74]2[CH:75]=[CH:76][CH:77]=[CH:78][C:73]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN(C=[O:90])C>>[CH:52]1([S:49]([NH:79][C:74]([C@@:73]2([NH:72][C:30]([C@H:20]3[N:19]4[CH2:29][C@H:22]([O:23][C:24]5[C:27]6[C:4](=[CH:5][CH:6]=[C:7]([CH:28]=6)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]6[O:37][C:15]([NH:16][C@@H:17]([CH:34]([CH3:35])[CH3:36])[C:18]4=[O:33])=[N:14][N:13]=6)[C:3]([CH2:1][CH3:2])=[CH:26][N:25]=5)[CH2:21]3)=[O:31])[CH2:78][C@H:77]2[CH:76]=[CH2:75])=[O:90])(=[O:51])=[O:50])[CH2:54][CH2:53]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67403254HCID 67403254, compoundHCID 136387747HCID 136387747, compound

Product 1

HCID 136387748HCID 136387748, compound

Procedure

(3R,5S,8S)-22-ethyl-8-isopropyl-7-oxo-2,27-dioxa-6,9,11,12,24-pentaazapentacyclo[16.6.2.13,6.110,13.021,25]octacosa-1(24),10,12,18,20,22,25-heptaene-5-carboxylic acid (from Step 3) was dissolved in DMF and to this solution was added Intermediate 2 followed by iPr2NEt (3.5 eq) and TBTU (1.09 eq). The resulting reaction mixture was stirred 12 h at RT and purified by reverse phase HPLC to give the title compound as a white solid. 1H NMR (600 MHz, DMSO-d6) δ 10.33 (s, 1H), 8.92 (s, 1H), 7.96 (d, J 9.7, 1H), 7.87 (d, J 8.6, 1H), 7.78 (s, 1H), 7.71 (s, 1H), 7.63 (dd, J 8.6, 1.5, 1H), 5.71 (s, 1H), 5.59 (m, 1H), 5.20 (d, J 17.2, 1H), 5.08 (d, J 10.2, 1H), 4.88 (d, J 10.8, 1H), 4.20 (dd, J 11.3, 7.2, 1H), 4.17 (t, J 9.6, 1H), 3.96 (dd, J 11.4, 3.4, 1H), 2.94-2.86 (m, 4H), 2.76 (m, 1H), 2.64 (m, 1H), 2.18-2.09 (m, 3H), 1.75-1.69 (m, 3H), 1.67-1.62 (m, 2H), 1.39-1.36 (m, 2H), 1.29-1.24 (m, 4H), 1.10-1.08 (m, 2H), 1.04-1.03 (m, 2H), 1.00 (t, J 6.6, 3H), 0.96 (d, J 6.6, 3H). MS (ES+) C36H45N7O7S requires: 719. Found: 720 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-78ee8180e5ef4bc9a840a7fe2cca5af7
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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